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Enantioselective synthesis of benzoindolizidine derivatives using chiral phase-transfer catalytic intramolecular domino aza-Michael addition/ alkylation† Jiajia Guo and Shouyun Yu*

Received 20th October 2014, Accepted 13th November 2014

An efficient and enantioselective strategy to synthesize benzoindolizidines from α,β-unsaturated amino ketones via domino intramolecular aza-Michael addition/alkylation was developed. These reactions were

DOI: 10.1039/c4ob02227k

enabled by cinchona alkaloid-derived quaternary ammonium salts as the phase-transfer catalyst. A variety of

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benzoindolizidines were prepared in good yields (up to 93%) and enantioselectivities (up to 92.8 : 7.2 er).

Introduction

Results and discussion

Phase-transfer catalysis (PTC) has long been recognized as a versatile methodology for organic synthesis in both industrial and academic laboratories.1 Asymmetric phase-transfer catalysis based on the use of structurally well-defined chiral, nonracemic catalysts has become a topic of great scientific interest, particularly in the last two decades.2 Recently, there have been successful applications of catalytic asymmetric synthesis using cinchona alkaloid-derived quaternary ammonium salts.2g The attachment of the bulky substituents to the bridgehead nitrogen leads to a quaternary ammonium structure of well-defined geometry in which the tetrahedral face of the ammonium nitrogen is blocked by a bulky subunit. The introduction of a bulky subunit at the 1-position of cinchona alkaloids enhances the stereoselectivity in asymmetric phasetransfer catalytic reactions.3 The most successful reaction catalysed by chiral phase-transfer catalyst is the asymmetric synthesis of α-amino acids by enantioselective alkylation of protected glycine derivatives.3a,b,4 Other reactions, such as Michael addition,5 aldol reaction,6 Mannich reaction,7 and Darzens reaction,8 are also achieved by chiral PTC. However, chiral PTC-catalyzed domino reactions are very rare and the results of the reported examples were disappointing in most cases.9

Recently, we have succeeded in the development of diastereoselective synthesis of epoxide-fused benzoquinolizidine derivatives using the intramolecular domino aza-Michael addition/ Darzens reaction from α,β-unsaturated amino aliphatic ketones (Scheme 1, pathway A).10 Interestingly, when the α,β-unsaturated aromatic ketone 1a was used instead of its aliphatic counterparts, the domino aza-Michael addition/ alkylation process was observed to give benzoindolizidine 3a diastereoselectively (Scheme 1, pathway B). This intriguing and promising result prompted us to investigate the enantioselective variant of this transformation. Firstly we tried a series of organocatalysts, which have been successfully used in the aza-Michael addition, including aminocatalysts and chiral Brønsted acids.11,12 We next turned our attention to phase-transfer catalyst (Table 1).13 Four cinchona alkaloid-based catalysts (2a, 2d–2f ) were examined, and the best result was obtained (60% yield, 21/79 er) with the cinchonidine-based catalyst 2a. Then the protecting groups of the hydroxy group were investigated (2a–2c). It was found that the protecting groups did not affect the reactivities of the catalysts and the protecting group-free catalyst 2a gave the best

State Key Laboratory of Analytical Chemistry for Life Science, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, China. E-mail: [email protected]; Fax: +86-25-83317761; Tel: +86-25-83594717 † Electronic supplementary information (ESI) available: Full experimental procedures, and characterization data for all the compounds. CCDC 1029009. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c4ob02227k

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Scheme 1

Aza-Michael-triggered domino reactions.

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Table 1

Organic & Biomolecular Chemistry Catalyst screeninga,b

Table 2

Optimization of reaction conditionsa

Entry

Base

Solvent

Temp/°C

Yieldb/%

Er

1 2 3 4 5 6 7 8 9 10 11 12 13 14c 15

KOH KOH KOH KOH KOH KOH KOH KOH KOH KOH K2CO3 NaOH CsOH KOH KOH

Toluene Toluene Toluene CHCl3 CH2Cl2 MTBE PhF PhCl m-Xylene Mesitylene m-Xylene m-Xylene m-Xylene m-Xylene m-Xylene

−20 −30 −40 −30 −30 −30 −30 −30 −30 −30 −30 −30 −30 −30 0

75 51 10 20 85 6 36 10 70 13 NR 10 60 97(91d) 83

84.0/16.0 88.7/11.3 74.6/25.4 56.0/44.0 59.6/40.4 57.4/42.6 60.2/39.8 62.0/38.0 88.1/11.9 76.2/23.8 — 85.2/14.8 88.0/12.0 88.4/11.6 67.6/32.4

a

A solution of 1a (0.10 mmol), 2g (0.01 mmol), and 5 M KOH 0.8 mL (4.0 mmol) in solvent (2 mL) at −30 °C was stirred for 48 h. b 1H NMR yield with CH2Br2 as an internal standard. c The reaction was carried out at −30 °C for 2 d, then stirred at 0 °C for 12 h. d Isolated yield.

a A solution of 1a (0.10 mmol), 2 (0.01 mmol) and 5 M KOH (0.2 mL, 1.0 mmol) in toluene (2 mL) at −30 °C was stirred for 48 h. b 1H NMR yield with CH2Br2 as an internal standard. c The reaction was carried out at −20 °C.

stereoinduction. We were pleased to find that the cinchonidine dimer-based catalyst 2g gave the most promising result (52% yield, 84/16 er). The Maruoka’s catalyst 2h was also tested; however, almost a racemic product 3a (54.0/46.0 er) was obtained despite with a decent yield (80% yield). (For more catalyst screening, see ESI.†) In order to improve the outcome of this reaction further, the reaction parameters were then screened, as shown in Table 2. We found that a better yield (75% NMR yield) was obtained when more KOH aqueous solution was used (entry 1, for more details, see ESI†). Temperature screening indicated that −30 °C was the most suitable temperature with 88.7/11.3 er (entries 1–3). Then different organic solvents were tested (entries 4–10), m-xylene proved to be the best solvent (70% yield, 88.1/11.9 er, entry 9). Three other bases were then evaluated. Unfortunately, none of them could yield a better result (entries 11–13). It was observed that the starting material 1a could be consumed completely to give the aza-Michael adduct quickly and the intramolecular alkylation was seen at −30 °C, which led to a low chemical yield. Finally, we found that after the α,β-unsaturated amino ketone 1a was consumed completely at −30 °C, the mixture was warmed up to 0 °C, and we obtained a higher yield and with a similar er value (97% NMR

1180 | Org. Biomol. Chem., 2015, 13, 1179–1186

yield and 91% isolated yield, 88.4/11.6 er, entry 14). When the reaction was performed at 0 °C for 2 days, the reaction could reach completion, but with a much lower er value (67.6/ 32.4 er, entry 15). It is noteworthy that only one diastereomer was observed in all cases. With the optimal conditions established, we explored the generality of this transformation. As shown in Table 3, a variety of α,β-unsaturated amino aromatic ketones were evaluated. To our delight, a series of benzoindolizidines 3a–3n with different functionalities could be prepared with good yields (up to 93%) and enantioselectivities (up to 92.8 : 7.2 er) using this domino process. All the products were isolated as one diastereomer exclusively based on 1H NMR analysis. α,β-unsaturated amino aliphatic ketones (1o) were also subjected to these conditions. However, the starting material was fully recovered. The structure and stereochemistry of 3l was established unambiguously by single crystal X-ray diffraction analysis.14 The rest of the products could also be assigned the same stereochemistry based on the assumption that all the reactions went through a similar pathway (Fig. 1).

Conclusions In summary, an efficient and enantioselective strategy to synthesize benzoindolizidines from α,β-unsaturated amino ketones via intramolecular domino aza-Michael addition/ alkylation was developed. A variety of benzoindolizidines with different functionalities were prepared in good yields (up to

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Organic & Biomolecular Chemistry Substrate scope for the domino aza-Michael/alkylationa,b

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Table 3

Paper

Fig. 1

X-ray crystallographic structure of 3l.

meter. Chemical shifts are expressed in parts per million ( ppm) with respect to the residual solvent peak. Coupling constants are reported in hertz (Hz), signal shapes and splitting patterns are indicated as follows: br, broad; s, singlet; d, doublet; t, triplet; q, quartet; m, multiplet. Infrared (IR) spectra were recorded on a Nicolet iS10 spectrophotometer and are reported as wavenumbers (cm−1). HRMS was measured using Agilent G 6500. Optical rotations were recorded on a A212000-T APIV/IW. General procedures for the domino reaction

a

A solution of 1 (0.10 mmol) and 5 M KOH 0.8 mL(4.0 mmol) in m-xylene (2 mL) was stirred at −30 °C for 1–3 days until 1 was consumed, then stirred at 0 °C for 6–24 h. b Isolated yield. c The reaction was carried out at −30 °C for 3–4 days.

93%) and enantioselectivities (up to 92.8 : 7.2 er) as one diastereomer.

Experimental General information Thin layer chromatography (TLC) was performed on EMD precoated plates (silica gel 60 F254, Art 5715). Optical rotations were recorded on a A212000-T APIV/IW. Column chromatography was performed on Silica Gel 60 (300–400 Mesh) using a forced flow of 0.5–1.0 bar. 1H NMR (400 MHz) and 13C NMR (100 MHz) were measured on a Bruker AVANCE III-400 spectro-

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Into a tube, 8.6 mg of phase transfer catalyst 2g (0.01 mmol, 0.1 eq.), 0.8 mL of 5.0 M KOH (4.0 mmol, 40 eq.) and 2.0 mL of m-xylene were add successively. Then the mixture was cooled to −30 °C and α,β-unsaturated amino ketone 1 (0.10 mmol) was added. The mixture was stirred for 1–2 d at −30 °C until 1 was consumed (monitoring with TLC), then heated up to 0 °C and stirred at this temperature for 6–24 h. After completion was indicated by TLC, 10 mL of H2O was added, and then extracted with DCM (10 mL × 3). The combined organic phases were washed with brine, dried over anhydrate Na2SO4 and filtered. The concentrated residue was purified by flash chromatography with a mixture of petroleum ether and ethyl acetate as the eluent to afford the pure products 3. If α,β-unsaturated amino ketone 1 was not consumed completely, it was stirred for 3–4 d at −30 °C, then products 3 were purified as per the same procedure. (1R,10bR)-1-Benzoyl-1,5,6,10b-tetrahydropyrrolo[2,1-a]isoquinolin-3(2H)-one (3a). 3a (26.4 mg, 91%, er 88.4/11.6) was prepared according to the general procedure as a yellow solid from 1a (32.8 mg, 0.10 mmol), PTC 2g (8.6 mg, 0.01 mmol) and 5.0 M KOH (0.8 mL, 4.0 mmol) in m-xylene (2.0 mL) at −30 °C for 48 h, then at 0 °C for 12 h. The er value was determined by HPLC analysis using a Chiralpak AD-H column (hexane–2-propanol = 90 : 10), λ = 254 nm, flow rate = 1.0 mL min−1, tR (major) = 17.24 min, tR (minor) = 27.50 min; [α]25 D = −64.3 (c 0.30, CHCl3). 1H NMR (400 MHz, CDCl3) δ 8.01 (s,

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1H), 7.99 (d, J = 1.2 Hz, 1H), 7.65 (t, J = 7.2 Hz, 1H), 7.53 (t, J = 7.6 Hz, 2H), 7.23–7.05 (m, 3H), 6.88 (d, J = 7.6 Hz, 1H), 5.56 (d, J = 8.0 Hz, 1H), 4.37 (ddd, J = 12.8, 6.0, 2.4 Hz, 1H), 4.17–4.03 (m, 1H), 3.22–3.09 (m, 1H), 3.07–2.96 (m, 1H), 2.92 (dd, J = 16.4, 9.6 Hz, 1H), 2.86–2.77 (m, 1H), 2.67 (ddd, J = 16.4, 10.8, 0.8 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ 198.97, 169.33, 136.51, 135.85, 134.12, 133.71, 129.37, 129.09, 128.70, 127.19, 127.06, 124.96, 57.72, 48.60, 37.67, 37.38, 28.65; FTIR (film): vmax 3024, 2920, 1670, 1594, 1578, 1459, 1440, 1423, 1354, 1305, 1261, 1246, 1210, 1158, 1018, 939, 898, 857, 762, 740, 706 cm−1; HRMS (ESI) calcd for C19H17NNaO2 (M + Na)+: 314.1157, found: 314.1155. (1R,10bR)-1-(4-Methylbenzoyl)-1,5,6,10b-tetrahydropyrrolo[2,1-a]isoquinolin-3(2H)-one (3b). 3b (25.7 mg, 84%, er 84.6/ 15.4) was prepared according to the general procedure as a yellow solid from 1b (34.2 mg, 0.10 mmol), PTC 2g (8.6 mg, 0.01 mmol), and 5.0 M KOH (0.8 mL, 4.0 mmol) in m-xylene (2.0 mL) at −30 °C for 72 h, then at 0 °C for 12 h. The er value was determined by HPLC analysis using a Chiralpak AD-H column (hexane–2-propanol = 90 : 10), λ = 254 nm, flow rate = 1.0 mL min−1, tR (major) = 21.74 min, tR (minor) = 30.07 min; 1 [α]25 D = −53.3 (c 0.42, CHCl3). H NMR (400 MHz, CDCl3) δ 7.91 (s, 1H), 7.88 (s, 1H), 7.33 (s, 1H), 7.31 (s, 1H), 7.21–7.06 (m, 3H), 6.87 (d, J = 7.6 Hz, 1H), 5.55 (d, J = 8.0 Hz, 1H), 4.37 (ddd, J = 12.8, 6.0, 2.4 Hz, 1H), 4.08 (td, J = 10.2, 8.0 Hz, 1H), 3.15 (td, J = 11.6, 4.0 Hz, 1H), 3.06–2.95 (m, 1H), 2.90 (dd, J = 16.4, 9.6 Hz, 1H), 2.86–2.78 (m, 1H), 2.66 (dd, J = 16.0, 11.2 Hz, 1H), 2.45 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 198.55, 169.44, 145.22, 136.58, 133.69, 133.41, 129.77, 129.34, 128.84, 127.14, 127.03, 125.00, 57.75, 48.46, 37.78, 37.36, 28.66, 21.75; FTIR (film): vmax 2924, 2854, 1671, 1605, 1564, 1457, 1438, 1417, 1358, 1307, 1255, 1182, 825, 753 cm−1; HRMS (ESI) calcd for C20H19NNaO2 (M + Na)+: 328.1313, found: 328.1311. (1R,10bR)-1-(4-Methoxybenzoyl)-1,5,6,10b-tetrahydropyrrolo[2,1-a]isoquinolin-3(2H)-one (3c). 3c (17.1 mg, 53%, er 82.9/ 17.1) was prepared according to the general procedure as a yellow solid from 1c (35.8 mg, 0.10 mmol), PTC 2g (8.6 mg, 0.01 mmol) and 5.0 M KOH (0.8 mL, 4.0 mmol) in m-xylene (2.0 mL) at−30 °C for 96 h. The er value was determined by HPLC analysis using a Chiralpak AD-H column (hexane– 2-propanol = 80 : 20), λ = 254 nm, flow rate = 1.0 mL min−1, tR (major) = 14.70 min, tR (minor) = 20.99 min; [α]25 D = −36.0 (c 0.99, CHCl3). 1H NMR (400 MHz, CDCl3) δ 7.99 (s, 1H), 7.97 (s, 1H), 7.21–7.06 (m, 3H), 7.00 (s, 1H), 6.98 (s, 1H), 6.87 (d, J = 8.0 Hz, 1H), 5.54 (d, J = 8.0 Hz, 1H), 4.37 (ddd, J = 12.8, 6.0, 2.0 Hz, 1H), 4.05 (td, J = 10.4, 8.0 Hz, 1H), 3.90 (s, 3H), 3.15 (td, J = 12.0, 4.2 Hz, 1H), 3.01 (ddd, J = 17.2, 11.2, 6.0 Hz, 1H), 2.92–2.77 (m, 2H), 2.67 (dd, J = 16.4, 10.8 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ 197.36, 169.53, 164.32, 136.62, 133.67, 131.09, 129.32, 128.92, 127.12, 127.02, 125.02, 114.25, 57.85, 55.63, 48.25, 37.86, 37.35, 28.67; FTIR (film): vmax 2916, 2849, 1665, 1595, 1573, 1510, 1458, 1419, 1358, 1307, 1246, 1169, 1020, 842, 762 cm−1; HRMS (ESI) calcd for C20H19NNaO3 (M + Na)+: 344.1263, found: 344.1262. (1R,10bR)-1-([1,1′-Biphenyl]-4-carbonyl)-1,5,6,10b-tetrahydropyrrolo[2,1-a]isoquinolin-3(2H)-one (3d). 3d (26.1 mg, 71%, er

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Organic & Biomolecular Chemistry

87.6/12.4) was prepared according to the general procedure as a pale yellow oil from 1d (40.4 mg, 0.10 mmol), PTC 2g (8.6 mg, 0.01 mmol) and 5.0 M KOH (0.8 mL, 4.0 mmol) in m-xylene (2.0 mL) at −30 °C for 96 h. The er value was determined by HPLC analysis using a Chiralpak AD-H column (hexane–2-propanol = 80 : 20), λ = 254 nm, flow rate = 1.0 mL min−1, tR (major) = 17.28 min, tR (minor) = 25.08 min; [α]25 D = −75.0 (c 1.00, CHCl3). 1H NMR (400 MHz, CDCl3) δ 8.08 (s, 1H), 8.06 (s, 1H), 7.76 (s, 1H), 7.73 (s, 1H), 7.65 (d, J = 1.6 Hz, 1H), 7.63 (s, 1H), 7.62–7.46 (m, 2H), 7.45–7.39 (m, 1H), 7.22–7.08 (m, 3H), 6.90 (d, J = 7.6 Hz, 1H), 5.58 (d, J = 8.0 Hz, 1H), 4.38 (ddd, J = 12.8, 6.0, 2.0 Hz, 1H), 4.19–4.06 (m, 1H), 3.17 (td, J = 12.0, 4.0 Hz, 1H), 3.07–2.98 (m, 1H), 2.94 (dd, J = 16.4, 10.0 Hz, 1H), 2.87–2.78 (m, 1H), 2.71 (dd, J = 16.4, 10.8 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ 198.53, 169.36, 146.85, 139.49, 136.54, 134.50, 133.72, 129.39, 129.33, 129.07, 128.57, 127.69, 127.33, 127.20, 127.08, 124.99, 57.77, 48.64, 37.75, 37.39, 28.68; FTIR (film): vmax 2920, 2847, 1672, 1601, 1457, 1434, 1416, 1254, 1192, 1006, 938, 851, 742, 696 cm−1; HRMS (ESI) calcd for C25H21NNaO2 (M + Na)+: 390.1470, found: 390.1466. (1R,10bR)-1-(2-Naphthoyl)-1,5,6,10b-tetrahydropyrrolo[2,1-a]isoquinolin-3(2H)-one (3e). 3e (31.2 mg, 91%, er 86.6/13.4) was prepared according to the general procedure as pale yellow oil from 1e (37.8 mg, 0.10 mmol), PTC 2g (8.6 mg, 0.01 mmol) and 5.0 M KOH (0.8 mL, 4.0 mmol) in m-xylene (2.0 mL) at −30 °C for 48 h, then at 0 °C for 24 h. The er value was determined by HPLC analysis using a Chiralpak AD-H column (hexane–2-propanol = 90 : 10), λ = 254 nm, flow rate = 1.0 mL min−1, tR (major) = 25.32 min, tR (minor) = 35.37 min; [α]25 D = −63.0 (c 1.00, CHCl3). 1H NMR (400 MHz, CDCl3) δ 8.47 (s, 1H), 8.10 (dd, J = 8.4, 1.0 Hz, 1H), 8.01–7.85 (m, 3H), 7.65 (t, J = 7.6 Hz, 1H), 7.58 (t, J = 7.6 Hz, 1H), 7.22–7.13 (m, 2H), 7.13–7.03 (m, 1H), 6.91 (d, J = 7.6 Hz, 1H), 5.61 (d, J = 7.6 Hz, 1H), 4.47–4.34 (m, 1H), 4.28 (dd, J = 18.8, 10.0 Hz, 1H), 3.17 (td, J = 12.0, 4.0 Hz, 1H), 3.10–2.92 (m, 2H), 2.84 (d, J = 16.0 Hz, 1H), 2.74 (dd, J = 16.4, 11.2 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ 198.95, 169.39, 136.56, 136.00, 133.73, 133.24, 132.52, 130.79, 129.76, 129.39, 129.19, 129.06, 127.88, 127.22, 127.21, 127.09, 125.01, 123.98, 57.90, 48.65, 37.92, 37.40, 28.70; FTIR (film): vmax 3048, 2922, 1670, 1625, 1595, 1457, 1434, 1418, 1264, 1233, 1178, 1124, 1034, 936, 903, 866, 811, 752, 727 cm−1; HRMS (ESI) calcd for C23H19NNaO2 (M + Na)+: 364.1313, found: 364.1310. (1R,10bR)-1-(4-Fluorobenzoyl)-1,5,6,10b-tetrahydropyrrolo[2,1-a]isoquinolin-3(2H)-one (3f ). 3f (27.1 mg, 88%, er 75.9/ 24.1) was prepared according to the general procedure as a pale yellow solid from 1f (34.6 mg, 0.10 mmol), PTC 2g (8.6 mg, 0.01 mmol) and 5.0 M KOH (0.8 mL, 4.0 mmol) in m-xylene (2.0 mL) at −30 °C for 36 h, then at 0 °C for 10 h. The er value was determined by HPLC analysis using a Chiralpak AD-H column (hexane–2-propanol = 80 : 20), λ = 254 nm, flow rate = 1.0 mL min−1, tR (major) = 10.40 min, tR (minor) = 1 18.47 min; [α]25 D = −34.2 (c 0.70, CHCl3). H NMR (400 MHz, CDCl3) δ 8.03 (dd, J = 8.4, 5.2 Hz, 2H), 7.25–7.04 (m, 5H), 6.85 (d, J = 7.6 Hz, 1H), 5.54 (d, J = 7.6 Hz, 1H), 4.38 (dd, J = 12.8,

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4.0 Hz, 1H), 4.05 (dd, J = 18.4, 10.0 Hz, 1H), 3.15 (td, J = 11.6, 4.0 Hz, 1H), 3.07–2.95 (m, 1H), 2.90–2.77 (m, 2H), 2.67 (dd, J = 16.4, 10.8 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ 197.41, 169.20, 166.33 (d, J = 256.8 Hz), 136.37, 133.73, 132.31 (d, J = 2.8 Hz), 131.47, 131.38, 129.44, 127.25, 127.07, 124.87, 116.43, 116.21, 57.76, 48.58, 37.62, 37.38, 28.65; FTIR (film): vmax 2921, 2847, 1707, 1677, 1594, 1506, 1460, 1419, 1357, 1307, 1257, 1204, 1152, 1033, 844, 809, 763, 739 cm−1; HRMS (ESI) calcd for C19H16FNNaO2 (M + Na)+: 332.1063, found: 332.1060. (1R,10bR)-1-(4-Chlorobenzoyl)-1,5,6,10b-tetrahydropyrrolo[2,1-a]isoquinolin-3(2H)-one (3g). 3g (30.3 mg, 93%, er 90.9/ 9.1) was prepared according to the general procedure as colorless oil from 1g (36.2 mg, 0.10 mmol), PTC 2g (8.6 mg, 0.01 mmol) and 5.0 M KOH (0.8 mL, 4.0 mmol) in m-xylene (2.0 mL) at −30 °C for 58 h, then at 0 °C for 24 h. The er value was determined by HPLC analysis using a Chiralpak AD-H column (hexane–2-propanol = 90 : 10), λ = 254 nm, flow rate = 1.0 mL min−1, tR (major) = 23.01 min, tR (minor) = 37.08 min; 1 [α]25 D = −77.4 (c 1.00, CHCl3). H NMR (400 MHz, CDCl3) δ 7.96–7.93 (m, 1H), 7.94–7.90 (m, 1H), 7.53–7.51 (m, 1H), 7.51–7.47 (m, 1H), 7.22–7.08 (m, 3H), 6.84 (d, J = 7.6 Hz, 1H), 5.54 (d, J = 7.6 Hz, 1H), 4.37 (ddd, J = 12.8, 6.0, 2.2 Hz, 1H), 4.09–3.99 (m, 1H), 3.20–3.09 (m, 1H), 3.00 (ddd, J = 17.2, 11.2, 6.0 Hz, 1H), 2.89 (dd, J = 16.4, 9.6 Hz, 1H), 2.85–2.78 (m, 1H), 2.66 (ddd, J = 16.4, 10.8, 1.2 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ 197.84, 169.14, 140.78, 136.31, 134.15, 133.73, 130.07, 129.45, 127.28, 127.09, 124.84, 57.74, 48.60, 37.55, 37.39, 28.64; FTIR (film): vmax 2920, 2857, 1675, 1587, 1495, 1457, 1416, 1355, 1306, 1247, 1090, 1010, 941, 828, 747 cm−1; HRMS (ESI) calcd for C19H16ClNNaO2 (M + Na)+: 348.0767, found: 348.0763. (1R,10bR)-1-(4-Bromobenzoyl)-1,5,6,10b-tetrahydropyrrolo[2,1-a]isoquinolin-3(2H)-one (3h). 3h (34.4 mg, 93%, er 82.8/ 17.2) was prepared according to the general procedure as a white solid from 1h (40.7 mg, 0.10 mmol), PTC 2g (8.6 mg, 0.01 mmol) and 5.0 M KOH (0.8 mL, 4.0 mmol) in m-xylene (2.0 mL) at −30 °C for 60 h, then at 0 °C for 24 h. The er value was determined by HPLC analysis using a Chiralpak AD-H column (hexane–2-propanol = 80 : 20), λ = 254 nm, flow rate = 1.0 mL min−1, tR (major) = 12.87 min, tR (minor) = 12.04 min; 1 [α]25 D = −45.6 (c 0.36, CHCl3). H NMR (400 MHz, CDCl3) δ 7.89–7.80 (m, 2H), 7.71–7.63 (m, 2H), 7.22–7.07 (m, 3H), 6.83 (d, J = 7.6 Hz, 1H), 5.53 (d, J = 7.6 Hz, 1H), 4.37 (ddd, J = 12.8, 6.0, 2.0 Hz, 1H), 4.04 (td, J = 10.4, 8.0 Hz, 1H), 3.15 (td, J = 11.8, 3.6 Hz, 1H), 3.00 (ddd, J = 17.0, 11.3, 6.0 Hz, 1H), 2.95–2.78 (m, 2H), 2.66 (ddd, J = 16.4, 10.8, 0.8 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ 198.06, 169.11, 136.30, 134.55, 133.73, 132.46, 130.13, 129.58, 129.45, 127.29, 127.09, 124.84, 57.73, 48.59, 37.55, 37.39, 28.64; FTIR (film): vmax 2924, 1852, 1674, 1583, 1459, 1418, 1392, 1356, 1247, 1201, 1173, 1069, 1007, 938, 896, 825, 766, 740 cm−1; HRMS (ESI) calcd for C19H16BrNNaO2 (M + Na)+: 392.0262, found: 392.0256. (1R,10bR)-1-(Furan-2-carbonyl)-1,5,6,10b-tetrahydropyrrolo[2,1-a]isoquinolin-3(2H)-one (3i). 3i (24.5 mg, 87%, er 77.0/ 23.0) was prepared according to the general procedure as a white solid from 1i (31.8 mg, 0.10 mmol), PTC 2g (8.6 mg,

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0.01 mmol) and 5.0 M KOH (0.8 mL, 4.0 mmol) in m-xylene (2.0 mL) at −30 °C for 36 h, then at 0 °C for 10 h. The er value was determined by HPLC analysis using a Chiralpak AD-H column (hexane–2-propanol = 80 : 20), λ = 254 nm, flow rate = 1.0 mL min−1, tR (major) = 11.21 min, tR (minor) = 14.06 min; 1 [α]25 D = −19.6 (c 0.93, CHCl3). H NMR (400 MHz, CDCl3) δ 7.67 (d, J = 1.2 Hz, 1H), 7.33 (d, J = 3.6 Hz, 1H), 7.23–7.08 (m, 3H), 6.92 (d, J = 7.6 Hz, 1H), 6.63 (dd, J = 3.6, 1.6 Hz, 1H), 5.44 (d, J = 8.0 Hz, 1H), 4.36 (ddd, J = 12.8, 6.0, 2.4 Hz, 1H), 3.92 (td, J = 10.4, 8.4 Hz, 1H), 3.14 (td, J = 11.6, 4.4 Hz, 1H), 3.05–2.96 (m, 1H), 2.92 (dd, J = 16.4, 9.6 Hz, 1H), 2.85–2.77 (m, 1H), 2.73 (ddd, J = 16.4, 10.4, 1.0 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ 187.71, 169.59, 152.12, 147.59, 136.33, 133.77, 129.35, 127.21, 127.01, 124.97, 118.98, 112.92, 57.35, 48.84, 37.37, 37.02, 28.61; FTIR (film): vmax 3115, 3103, 2917, 2859, 1677, 1659, 1563, 1465, 1416, 1399, 1355, 1305, 1279, 1170, 1153, 1058, 1033, 998, 924, 879, 797, 771, 759, 737 cm−1; HRMS (ESI) calcd for C17H15NNaO3 (M + Na)+: 304.0950, found: 304.0948. (1R,10bR)-1-(Thiophene-2-carbonyl)-1,5,6,10b-tetrahydropyrrolo[2,1-a]isoquinolin-3(2H)-one (3j). 3j (27.1 mg, 91%, er 84.2/15.8) was prepared according to the general procedure as a white solid from 1j (33.4 mg, 0.10 mmol), PTC 2g (8.6 mg, 0.01 mmol) and 5.0 M KOH (0.8 mL, 4.0 mmol) in m-xylene (2.0 mL) at −30 °C for 72 h, then at 0 °C for 24 h. The er value was determined by HPLC analysis using a Chiralpak AD-H column (hexane–2-propanol = 90 : 10), λ = 254 nm, flow rate = 1.0 mL min−1, tR (major) = 19.13 min, tR (minor) = 32.71 min; 1 [α]25 D = −48.3 (c 0.56, CHCl3). H NMR (400 MHz, CDCl3) δ 7.78 (dd, J = 4.8, 1.0 Hz, 1H), 7.73 (dd, J = 3.6, 1.0 Hz, 1H), 7.23–7.07 (m, 4H), 6.91 (d, J = 7.6 Hz, 1H), 5.48 (d, J = 8.0 Hz, 1H), 4.37 (ddd, J = 12.8, 6.0, 2.4 Hz, 1H), 3.99–3.88 (m, 1H), 3.19–3.08 (m, 1H), 3.06–2.95 (m, 1H), 2.91 (dd, J = 16.4, 9.6 Hz, 1H), 2.85–2.71 (m, 2H); 13C NMR (100 MHz, CDCl3) δ 191.76, 169.39, 143.39, 136.26, 135.50, 133.70, 133.06, 129.39, 128.71, 127.25, 127.06, 125.01, 57.85, 49.84, 37.96, 37.34, 28.64; FTIR (film): vmax 3413, 2913, 2857, 1665, 1653, 1578, 1490, 1459, 1424, 1353, 1306, 1274, 1210, 1152, 1031, 992, 943, 805, 746 cm−1; HRMS (ESI) calcd for C17H15NNaO2S (M + Na)+: 320.0721, found: 320.0718. (1R,10bR)-1-Picolinoyl-1,5,6,10b-tetrahydropyrrolo[2,1-a]isoquinolin-3(2H)-one (3k). 3k (26.1 mg, 89%, er 81.7/18.3) was prepared according to the general procedure as a yellow solid from 1k (32.9 mg, 0.10 mmol), PTC 2g (8.6 mg, 0.01 mmol) and 5.0 M KOH (0.8 mL, 4.0 mmol) in m-xylene (2.0 mL) at −30 °C for 48 h, then at 0 °C for 24 h. The er value was determined by HPLC analysis using a Chiralpak AD-H column (hexane–2-propanol = 80 : 20), λ = 254 nm, flow rate = 1.0 mL min−1, tR (minor) = 15.92 min, tR (major) = 19.47 min; [α]25 D = −47.2 (c 0.86, CHCl3). 1H NMR (400 MHz, CDCl3) δ 8.69 (d, J = 4.0 Hz, 1H), 8.20 (d, J = 8.0 Hz, 1H), 7.92 (td, J = 7.6, 1.6 Hz, 1H), 7.54 (ddd, J = 7.6, 4.8, 1.2 Hz, 1H), 7.22–7.06 (m, 3H), 6.99 (d, J = 7.2 Hz, 1H), 5.48 (d, J = 7.6 Hz, 1H), 4.76–7.06 (m, 1H), 4.34 (ddd, J = 12.8, 6.0, 2.4 Hz, 1H), 3.17 (td, J = 11.6, 4.4 Hz, 1H), 3.12–2.96 (m, 2H), 2.88–2.74 (m, 1H), 2.69–2.54 (m, 1H); 13 C NMR (100 MHz, CDCl3) δ 200.46, 170.29, 152.15, 149.36, 137.17, 136.79, 133.88, 129.21, 127.82, 127.05, 126.89, 125.03,

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122.80, 57.46, 47.31, 37.52, 36.97, 28.58; FTIR (film): vmax 3422, 2910, 2852, 1692, 1664, 1583, 1459, 1424, 1356, 1305, 1274, 1245, 1150, 994, 943, 803, 745 cm−1; HRMS (ESI) calcd for C18H16N2NaO2 (M + Na)+: 315.1109, found: 315.1108. (1R,10bR)-1-Benzoyl-9-bromo-1,5,6,10b-tetrahydropyrrolo[2,1-a]isoquinolin-3(2H)-one (3l). 3l (32.0 mg, 86%, er 92.8/ 7.2) was prepared according to the general procedure as a pale green solid from 1l (40.6 mg, 0.10 mmol), PTC 2g (8.6 mg, 0.01 mmol) and 5.0 M KOH (0.8 mL, 4.0 mmol) in m-xylene (2.0 mL) at −30 °C for 96 h. The er value was determined by HPLC analysis using a Chiralpak AD-H column (hexane–2propanol = 80 : 20), λ = 254 nm, flow rate = 1.0 mL min−1, tR (major) = 10.22 min, tR (minor) = 15.88 min; [α]25 D = +24.0 (c 1.02, CHCl3). 1H NMR (400 MHz, CDCl3) δ 8.00 (s, 1H), 7.98 (d, J = 1.6 Hz, 1H), 7.67 (t, J = 7.4 Hz, 1H), 7.55 (t, J = 7.6 Hz, 2H), 7.30 (dd, J = 8.2, 1.8 Hz, 1H), 7.06–7.00 (m, 2H), 5.53 (d, J = 7.6 Hz, 1H), 4.38 (ddd, J = 12.8, 6.0, 2.0 Hz, 1H), 4.06 (td, J = 10.4, 7.6 Hz, 1H), 3.11 (td, J = 12.0, 4.0 Hz, 1H), 2.93 (ddd, J = 16.4, 10.8, 6.2 Hz, 2H), 2.82–2.73 (m, 1H), 2.66 (dd, J = 16.4, 10.8 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ 198.47, 169.21, 138.62, 135.60, 134.24, 132.74, 131.02, 130.37, 129.14, 128.75, 128.03, 120.59, 57.08, 48.53, 37.44, 37.12, 28.26; FTIR (film): vmax 2921, 2847, 1686, 1671, 1593, 1574, 1447, 1425, 1357, 1296, 1255, 1146, 997, 946, 893, 867, 817, 784, 701, 661, 641 cm−1; HRMS (ESI) calcd for C19H16BrNNaO2 (M + Na)+: 392.0262, found: 392.0258. (1R,10bR)-1-Benzoyl-9-nitro-1,5,6,10b-tetrahydropyrrolo[2,1-a]isoquinolin-3(2H)-one (3m). 3m (25.2 mg, 75%, er 92.1/7.9) was prepared according to the general procedure as a yellow solid from 1m (37.3 mg, 0.10 mmol), PTC 2g (8.6 mg, 0.01 mmol) and 5.0 M KOH (0.8 mL, 4.0 mmol) in m-xylene (2.0 mL) at −30 °C for 72 h, then at 0 °C for 24 h. The er value was determined by HPLC analysis using a Chiralpak AD-H column (hexane–2-propanol = 80 : 20), λ = 254 nm, flow rate = 1.0 mL min−1, tR (major) = 16.49 min, tR (minor) = 24.63 min; 1 [α]25 D = +27.7 (c 0.62, CHCl3); H NMR (400 MHz, CDCl3) δ 8.04 (dd, J = 8.4, 2.0 Hz, 1H), 8.01 (s, 1H), 7.99 (d, J = 1.6 Hz, 1H), 7.80 (d, J = 1.6 Hz, 1H), 7.71–7.63 (m, 1H), 7.55 (t, J = 7.6 Hz, 2H), 7.35 (d, J = 8.4 Hz, 1H), 5.62 (d, J = 7.6 Hz, 1H), 4.48–4.38 (m, 1H), 4.14–4.03 (m, 1H), 3.22–2.90 (m, 4H), 2.71 (ddd, J = 16.8, 10.4, 0.8 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ 198.17, 169.26, 146.97, 141.45, 138.09, 135.42, 134.43, 130.49, 129.21, 128.76, 122.12, 120.47, 57.23, 48.49, 37.33, 36.70, 28.93; FTIR (film): vmax 1684, 1670, 1590, 1522, 1446, 1420, 1347, 1277, 1258, 1206, 1143, 903, 834, 765, 750 cm−1; HRMS (ESI) calcd for C19H16N2NaO4 (M + Na)+: 359.1008, found: 359.1004. (1R,10bR)-1-Benzoyl-8-methoxy-1,5,6,10b-tetrahydropyrrolo[2,1-a]isoquinolin-3(2H)-one (3n). 3n (28.0 mg, 87%, er 69.0/ 31.0) was prepared according to the general procedure as a white solid from 1n (35.8 mg, 0.10 mmol), PTC 2g (8.6 mg, 0.01 mmol) and 5.0 M KOH (0.8 mL, 4.0 mmol) in m-xylene (2.0 mL) at −30 °C for 42 h, then at 0 °C for 24 h. The er value was determined by HPLC analysis using a Chiralpak AD-H column (hexane–2-propanol = 80 : 20), λ = 254 nm, flow rate = 1.0 mL min−1, tR (major) = 12.01 min, tR (minor) = 16.46 min; 1 [α]25 D = −28.1 (c 0.37, CHCl3). H NMR (400 MHz, CDCl3) δ 8.00

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(s, 1H), 7.98 (d, J = 1.2 Hz, 1H), 7.65 (t, J = 7.4 Hz, 1H), 7.53 (t, J = 7.6 Hz, 2H), 6.84–6.76 (m, 1H), 6.72–6.62 (m, 2H), 5.49 (d, J = 7.6 Hz, 1H), 4.36 (ddd, J = 12.8, 6.0, 2.0 Hz, 1H), 4.09–4.00 (m, 1H), 3.76 (s, 3H), 3.13 (td, J = 11.8, 3.4 Hz, 1H), 3.05–2.94 (m, 1H), 2.89 (dd, J = 16.4, 9.6 Hz, 1H), 2.78 (d, J = 16.0 Hz, 1H), 2.67 (dd, J = 16.4, 10.8 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ 199.13, 169.37, 158.44, 135.91, 135.11, 134.09, 129.07, 128.67, 126.12, 113.89, 113.28, 57.47, 55.28, 48.94, 37.71, 37.26, 29.00; FTIR (film): vmax 2924, 2887, 2855, 1676, 1616, 1596, 1577, 1501, 1439, 1419, 1360, 1334, 1247, 1207, 1158, 1127, 1034, 1002, 802, 781, 709 cm−1; HRMS (ESI) calcd for C20H19NNaO3 (M + Na)+: 344.1263, found: 344.1263.

Acknowledgements This work was financially supported by 863 program (2013AA092903), the National Natural Science Foundation of China (21102072, 21272113) and Research Fund for the Doctoral Program of Higher Education of China (20110091120008).

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alkylation.

An efficient and enantioselective strategy to synthesize benzoindolizidines from α,β-unsaturated amino ketones via domino intramolecular aza-Michael a...
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