One-pot, Catalytic Asymmetric Reductive Bischler-Napieralski-Type Reaction of Amides: An Enantioselective Entrance to Biologically Active 1-Substituted Tetrahydroisoquinolines

doi:10.6023/A25120419

Abstract

Herein, we report the one-pot, catalytic asymmetric reductive Bischler-Napieralski-type reaction of amides as the first demonstration of a new strategy for the asymmetric reductive transformation of amides, which allowed for the one-pot, enantioselective access to tetrahydroisoquinoline (THIQ). The method features a tandem sequence involving the Tf₂O/2-F-Pyr.-promoted Bischler-Napieralski dehydracyclization and an aqueous Noyori-type catalytic asymmetric transfer hydrogenation (CATH). By this one-pot method, a variety of THIQ derivatives were synthesized in high yields and in excellent enantioselectivities. This protocol accommodates N-arylethyl aromatic amides bearing either electron-donating or electron-withdrawing groups on the acyl moiety, and N-arylethyl aliphatic amides. The synthetic utility of this methodology was demonstrated via the efficient, catalytic enantioselective synthesis of four alkaloids: (S)-salsolidine, (S)-laudanosine, (S)-xylopinine, and (S)-N-norlaudanidine, and medicinal agent ACT-335827. Additionally, formal syntheses of alkaloid (S)-cryptostyline III and medicinal agents such as almorexant were achieved.

Key words: amides, amide activation, tetrahydroisoquinolines, alkaloids, reductive Bischler-Napieralski-type reaction, catalytic asymmetric transfer hydrogenation, catalytic asymmetric synthesis

Cite this article

Guangsheng Lu, Zeng Han, Jianliang Ye, Peiqiang Huang. One-pot, Catalytic Asymmetric Reductive Bischler-Napieralski-Type Reaction of Amides: An Enantioselective Entrance to Biologically Active 1-Substituted Tetrahydroisoquinolines[J]. Acta Chimica Sinica, 2026, 84(4): 476-483.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 7

Scheme 1. Strategies for the direct, catalytic asymmetric reductive functionalization of amides

Figure 1. Representative 1-substituted tetrahydroisoquinoline alkaloids and medicinal agents

Scheme 2. Initial attempts for a one-pot protocol integrating Bischler-Napieralski reaction with Noyori’s CATH

Entry	Variation from standard condition	Yield^a/%	ee^b/%
1	none	96	94
2	1 mol% (R,R)-NC	86	93
3	0.5 mol% (R,R)-NC	52	90
4	0.1 mol% (R,R)-NC	34	92
5	no Bi(OTf)₃	40	89
6	no AgSbF₆	33	91
7	3 mol% AgSbF₆, 6 mol% Bi(OTf)₃	65	89
8	2 mol% AgSbF₆, 4 mol% Bi(OTf)₃	45	91
9	20 equiv. HCOONa	73	90
10	10 equiv. HCOONa	65	89
11	40 equiv. HCOONa	93	92
12	HCOOK instead of HCOONa	13	90
13	HCOOLi instead of HCOONa	8	90
14	HCOONH₄ instead of HCOONa	49	89
15	r.t. for 18 h	85	92

Table 1. Optimization of reaction conditions

Table 2. Scope of amidesa

Scheme 3. One-step synthesis and formal synthesis of natural products and medicinal agents

Scheme 4. Synthesis of alkaloid (S)-N-norlaudanidine

References 30

[1]	(a) Wender, P. A.; Verma, V. A.; Paxton, T. J.; Pillow, T. H. Acc. Chem. Res. 2008, 41, 40. doi: 10.1021/ar700155p pmid: 28791118
	(b) Li, C.-J.; Trost, B. M. Proc. Nat. Acad. Sci. 2008, 105, 13197. doi: 10.1073/pnas.0804348105 pmid: 28791118
	(c) Newhouse, T.; Baran, P. S.; Hoffmann, R. W. Chem. Soc. Rev. 2009, 38, 3010. doi: 10.1039/b821200g pmid: 28791118
	(d) Hayashi, Y. Chem. Sci. 2016, 7, 866. doi: 10.1039/c5sc02913a pmid: 28791118
	(e) Huang, P.-Q. In Efficiency in Natural Product Total Synthesis, Eds.: Huang,P.-Q.; YaoZ.-J.; HsungR. P., John Wiley &Sons, Inc., 2018, Chapters 1—2. pmid: 28791118
	(f) Gao, Y.; Ma, D. W. Acc. Chem. Res. 2021, 54, 569. doi: 10.1021/acs.accounts.0c00727 pmid: 28791118
	(g) Hayashi, Y. Acc. Chem. Res. 2021, 54, 1385. doi: 10.1021/acs.accounts.0c00803 pmid: 28791118
	(h) Kar, S.; Sanderson, H.; Roy, K.; Benfenati, E.; Leszczynski, J. Chem. Rev. 2022, 122, 3637. doi: 10.1021/acs.chemrev.1c00631 pmid: 28791118
	(i) Zhao, Y.-C.; Yu, B. Acta Chim. Sinica 2025, 83, 1397 (in Chinese). doi: 10.6023/A25070247 pmid: 28791118
	(赵雅宸, 俞飚, 化学学报, 2025, 83, 1397). doi: 10.6023/A25070247 pmid: 28791118
	(j) Chen, R.; Liu, Y.; Ding, H. Org. Chem. Front. 2025, 12, 2415. doi: 10.1039/D4QO02276A pmid: 28791118
	(k) Jiang, P.-Y.; Wu, S.; Wang, J.; Xiang, S.-H.; Tan, B. Org. Chem. Front. 2025, 12, 4126. for selected recent examples, see: pmid: 28791118
	(l) Gan, K.-J.; Zhu, Y.; Shi, G.; Wu, C.; Ni, F.-Q.; Zhao, L.-H.; Dou, X.; Zhang, Z.; Lu, H.-H. Chin. J. Chem. 2025, 43, 79. doi: 10.1002/cjoc.v43.1 pmid: 28791118
	(m) Zuo, H.; Hu, Y.; Qiao, X.; Zhang, Y.; Wang, S. Acta Chim. Sinica 2025, 83, 981 (in Chinese). doi: 10.6023/A25050159 pmid: 28791118
	(左恒昕宇, 虎亚光, 乔霞, 张野, 王少华, 化学学报, 2025, 83, 981.) doi: 10.6023/A25050159 pmid: 28791118
[2]	(a) Falmagne, J.-B.; Escudero, J.; Taleb-Sahraoui, S.; Ghosez, L. Angew. Chem. Int. Ed. 1981, 20, 879. doi: 10.1002/anie.v20:10
	(b) Ghosez, L. Tetrahedron 2019, 75, 130345. doi: 10.1016/j.tet.2019.05.024
[3]	For selected examples, see: (a) Bechara, W. S.; Pelletier, G.; Charette, A. B. Nat. Chem. 2012, 4, 228. doi: 10.1038/nchem.1268
	(b) Barbe, G.; Charette, A. B. J. Am. Chem. Soc. 2008, 130, 1.
	(c) Pelletier, G.; Bechara, W. S.; Charette, A. B. J. Am. Chem. Soc. 2010, 132, 12817. doi: 10.1021/ja105194s
	(d) Charette, A. B.; Grenon, M. Can. J. Chem. 2001, 79, 1694. doi: 10.1139/v01-150
[4]	For selected examples, see: (a) White, K. L.; Mewald, M.; Movassaghi, M. J. Org. Chem. 2015, 80, 7403. doi: 10.1021/acs.joc.5b01023 pmid: 17076488
	(b) Movassaghi, M.; Hill, M. D. Org. Lett. 2008, 10, 3485. doi: 10.1021/ol801264u pmid: 17076488
	(c) Movassaghi, M.; Hill, M. D.; Ahmad, O. K. J. Am. Chem. Soc. 2007, 129, 10096. pmid: 17076488
	(d) Movassaghi, M.; Hill, M. D. J. Am. Chem. Soc. 2006, 128, 14254. pmid: 17076488
	(e) Medley, J. W.; Movassaghi, M. J. Org. Chem. 2009, 74, 1341. doi: 10.1021/jo802355d pmid: 17076488
[5]	For reviews, see: (a) Pace, V.; Holzer, W. Aust. J. Chem. 2013, 66, 507. doi: 10.1071/CH13042
	(b) Pace, V.; Holzer, W.; Olofsson, B. Adv. Synth. Catal. 2014, 356, 3697. doi: 10.1002/adsc.v356.18
	(c) Volkov, A.; Tinnis, F.; Slagbrand, T.; Trillo, P.; Adolfsson, H. Chem. Soc. Rev. 2016, 45, 6685. doi: 10.1039/C6CS00244G
	(d) Kaiser, D.; Bauer, A.; Lemmerer, M.; Maulide, N. Chem. Soc. Rev. 2018, 47, 7899. doi: 10.1039/C8CS00335A
	(e) Sato, T.; Yoritate, M.; Tajima, H.; Chida, N. Org. Biomol. Chem. 2018, 16, 3864. doi: 10.1039/C8OB00733K
	(f) Matheau-Raven, D.; Gabriel, P.; Leitch, J. A.; Almehmadi, Y. A.; Yamazaki, K.; Dixon, D. J. ACS Catal. 2020, 10, 8880. doi: 10.1021/acscatal.0c02377
	(g) Tahara, A.; Nagashima, H. Tetrahedron Lett. 2020, 61, 151423. doi: 10.1016/j.tetlet.2019.151423
	(h) Czerwiński, P. J.; Furman, B. Trends Chem. 2020, 2, 782. doi: 10.1016/j.trechm.2020.07.001
	(i) Czerwinski, P. J.; Furman, B. Front. Chem. 2021, 9, 655849. doi: 10.3389/fchem.2021.655849
	(j) Huang, H.; Kang, J. Y. Synthesis 2022, 54, 1157. doi: 10.1055/a-1679-8205
	(k) Luo, Y. Sci. Sin. Chim. 2023, 53, 129, corrigendum: Luo, Y. Sci. Sin. Chim. 2024, 54, 968 (in Chinese). doi: 10.1360/SSC-2023-0203
	(罗艳龙, 中国科学:化学, 2023, 53, 129, 勘误: 罗艳龙, 中国科学:化学, 2024, 54, 968).
	(l) Ou, W.; Huang, P.-Q. Acc. Chem. Res. 2025, 58, 2332. doi: 10.1021/acs.accounts.5c00366
[6]	For selected examples, see: (a) Yasui, S.; Aoki, S.; Okamura, T.; Sato, T. Chem. Lett. 2025, 54, upaf094. pmid: 20672260
	(b) Iwamoto, S.; Nakano, R.; Sasaki, K.; Kobayashi, S.; Taira, Y.; Takei, K.; Kawakita, R.; Tokuyama, A.; Nakamura, H.; Tomoike, M.; Kawahara, R.; Murase, A.; Simizu, S.; Chida, N.; Okamura, T.; Sato, T. Angew. Chem. Int. Ed. 2025, 64, e202508062. doi: 10.1002/anie.v64.29 pmid: 20672260
	(c) Sugiyama, Y.; Yamada, K.; Kaneko, D.; Kusagawa, Y.; Okamura, T.; Sato, T. Angew. Chem. Int. Ed. 2024, 63, e202317290. doi: 10.1002/anie.v63.6 pmid: 20672260
	(d) Iwamoto, S.; Tokuyama, A.; Hiraoka, S.; Takei, K.; Matsuzaka, K.; Matsumoto, T.; Chida, N.; Sato, T. Bull. Chem. Soc. Jpn. 2023, 96, 529. doi: 10.1246/bcsj.20230088 pmid: 20672260
	(e) Iiyama, S.; Mizutani, K.; Sato, T. Chem. Lett. 2023, 52, 682. doi: 10.1246/cl.230245 pmid: 20672260
	(f) Yoritate, M.; Takahashi, Y.; Tajima, H.; Ogihara, C.; Yokoyama, T.; Soda, Y.; Oishi, T.; Sato, T.; Chida, N. J. Am. Chem. Soc. 2017, 139, 18386. doi: 10.1021/jacs.7b10944 pmid: 20672260
	(g) Shirokane, K.; Kurosaki, Y.; Sato, T.; Chida, N. Angew. Chem. Int. Ed. 2010, 49, 6369. doi: 10.1002/anie.201001127 pmid: 20672260
[7]	For selected examples, see: (a) Pijper, B.; Martin, R.; Huertas-Alonso, A. J.; Linares, M. L.; Lopez, E.; Llaveria, J.; Diaz-Ortiz, A.; Dixon, D. J.; de la Hoz, A.; Alcazar, J. Org. Lett. 2024, 26, 2724. doi: 10.1021/acs.orglett.3c01390 pmid: 25399919
	(b) Miller, A. A. M.; Biallas, P.; Shennan, B. D. A.; Dixon, D. J. Angew. Chem. Int. Ed. 2024, 63, e202314308. doi: 10.1002/anie.v63.2 pmid: 25399919
	(c) Matheau-Raven, D.; Dixon, D. J. Angew. Chem. Int. Ed. 2021, 60, 19725. doi: 10.1002/anie.202107536 pmid: 25399919
	(d) Fuentes de Arriba, A. L.; Lenci, E.; Sonawane, M.; Formery, O.; Dixon, D. J. Angew. Chem. Int. Ed. 2017, 56, 3655. doi: 10.1002/anie.201612367 pmid: 25399919
	(e) Gregory, A. W.; Chambers, A.; Hawkins, A.; Jakubec, P.; Dixon, D. J. Chem.-Eur. J. 2015, 21, 111. doi: 10.1002/chem.201405256 pmid: 25399919
[8]	For catalytic asymmetric reductive transformations, see: (a) Ji, K.-L.; He, S.-F.; Xu, D.-D.; He, W.-X.; Zheng, J.-F.; Huang, P.-Q. Angew. Chem. Int. Ed. 2023, 62, e202302832. doi: 10.1002/anie.v62.25 pmid: 31479277
	(b) Xu, F.-F.; Chen, J.-Q.; Shao, D.-Y.; Huang, P.-Q. Nat. Commun. 2023, 14, 6251. doi: 10.1038/s41467-023-41846-x pmid: 31479277
	(c) Chen, H.; Wu, Z.-Z.; Shao, D.-Y.; Huang, P.-Q. Sci. Adv. 2022, 8, eade3431. pmid: 31479277
	(d) Chen, D.-H.; Sun, W.-T.; Zhu, C.-J.; Lu, G.-S.; Wu, D.-P.; Wang, A.-E; Huang, P.-Q. Angew. Chem. Int. Ed. 2021, 60, 8827. doi: 10.1002/anie.v60.16 pmid: 31479277
	(e) Xu, Z.; Wang, X.-G.; Wei, Y.-H.; Ji, K.-L.; Zheng, J.-F.; Ye, J.-L.; Huang, P.-Q. Org. Lett. 2019, 21, 7587. doi: 10.1021/acs.orglett.9b02862 pmid: 31479277
	For selected non-asymmetric transformations, see:(f) Weng, Z.-Y.; Li, Y.-Q.; He, W.-X.; Chen, Z.-Y.; Huang, P.-Q. CCS Chem. 2026, doi: 10.31635/ccschem.025.202506810. pmid: 31479277
	(g) Liu, M.-H.; Sun, W.-T.; Yang, A.-Q.; Wang, Z.; Chang, Z.; Wang, A.-E.; Huang, P.-Q. Sci. China Chem. 2026, 69, 332. doi: 10.1007/s11426-025-2935-3 pmid: 31479277
	(h) Xu, Y.-P.; Ruan, Y.; Zheng, J.-F.; Huang, P.-Q. Chin. J. Org. Chem. 2025, 45, 988 (in Chinese) doi: 10.6023/cjoc202408032 pmid: 31479277
	(徐业鹏, 阮义, 郑剑峰, 黄培强, 有机化学, 2025, 45, 988.) doi: 10.6023/cjoc202408032 pmid: 31479277
	(i) Chen, L.-N.; Jin, Z.-K.; Ye, J.-L.; Huang, P.-Q. Arkivoc 2024, 202412191. pmid: 31479277
	(j) Han, F.; Lu, G.-S.; Wu, D.-P.; Huang, P.-Q. Sci. China Chem. 2023, 66, 1094. doi: 10.1007/s11426-022-1501-y pmid: 31479277
	(k) He, Q.; Li, J.; Yu, S.-J.; Wu, D.-P.; Ye, J.-L.; Huang, P.-Q. Acta Chim. Sinica 2023, 81, 1265 (in Chinese). doi: 10.6023/A23050226 pmid: 31479277
	(何倩, 李杰, 喻思佳, 吴东坪, 叶剑良, 黄培强, 化学学报, 2023, 81, 1265.) doi: 10.6023/A23050226 pmid: 31479277
	(l) Huang, P.-Q.; Ou, W.; Han, F. Chem. Commun. 2016, 52, 11967. doi: 10.1039/C6CC05318A pmid: 31479277
	(m) Xiao, K.-J.; Luo, J.-M.; Ye, K.-Y.; Wang, Y.; Huang, P.-Q. Angew. Chem. Int. Ed. 2010, 49, 3037. doi: 10.1002/anie.v49:17 pmid: 31479277
[9]	For selected examples, see: (a) Pace, V.; de la Vega-Hernandez, K.; Urban, E.; Langer, T. Org. Lett. 2016, 18, 2750. doi: 10.1021/acs.orglett.6b01226
	(b) Miele, M.; Castoldi, L.; Beccalli, E.; Pace, V. Adv. Synth. Catal. 2024, 366, 2277. doi: 10.1002/adsc.v366.10
	(c) Senatore, R.; Ielo, L.; Monticelli, S.; Castoldi, L.; Pace, V. Synthesis 2019, 51, 2792. doi: 10.1055/s-0037-1611549
	(d) Touqeer, S.; Senatore, R.; Malik, M.; Urban, E.; Pace, V. Adv. Synth. Catal. 2020, 362, 5056. doi: 10.1002/adsc.v362.22
[10]	For selected examples, see: (a) Szczesniak, P.; Stecko, S.; Staszewska-Krajewska, O.; Furman, B. Tetrahedron 2014, 70, 1880. doi: 10.1016/j.tet.2014.01.039
	(b) Szczesniak, P.; Maziarz, E.; Stecko, S.; Furman, B. J. Org. Chem. 2015, 80, 3621. doi: 10.1021/acs.joc.5b00335
[11]	For selected examples, see: (a) Li, Z.; Zhao, F.; Ou, W.; Huang, P.-Q.; Wang, X. Angew. Chem. Int. Ed. 2021, 60, 26604. doi: 10.1002/anie.v60.51
	(b) Jiao, J.-W.; Wang, X.-M. Angew. Chem. Int. Ed. 2021, 60, 17088. doi: 10.1002/anie.v60.31
	(c) Li, J.; He, Y.; Jiang, F.; Wang, X. Green Chem. 2023, 25, 9080. doi: 10.1039/D3GC03193D
[12]	For selected examples, see: (a) Fang, W.; Luo, Z.-W.; Wang, Y.-C.; Zhou, W.; Li, L.; Chen, Y.; Zhang, X.; Dai, M.; Dai, J.-J. Angew. Chem. Int. Ed. 2024, 63, e202317570. doi: 10.1002/anie.v63.14 pmid: 22770123
	(b) Lu, J. X.; Li, Z. H.; Deng, L. J. Am. Chem. Soc. 2024, 146, 4357. doi: 10.1021/jacs.3c14517 pmid: 22770123
	(c) Shi, Q.; Liu, W. H. Angew. Chem. Int. Ed. 2023, 62, e202309567. doi: 10.1002/anie.v62.37 pmid: 22770123
	(d) Tang, Z.; Mo, K.; Ma, X.; Huang, J.; Zhao, D. Angew. Chem. Int. Ed. 2022, 61, e202208089. doi: 10.1002/anie.v61.36 pmid: 22770123
	(e) Agrawal, T.; Perez-Morales, K. D.; Cort, J. A.; Sieber, J. D. J. Org. Chem. 2022, 87, 6387. doi: 10.1021/acs.joc.2c00131 pmid: 22770123
	(f) Trillo, P.; Slagbrand, T.; Adolfsson, H. Angew. Chem. Int. Ed. 2018, 57, 12347. doi: 10.1002/anie.201807735 pmid: 22770123
	(g) Cheng, C.; Brookhart, M. J. Am. Chem. Soc. 2012, 134, 11304. doi: 10.1021/ja304547s pmid: 22770123
	(h) Motoyama, Y.; Aoki, M.; Takaoka, N.; Aoto, R.; Nagashima, H. Chem. Commun. 2009, 1574. pmid: 22770123
	For a recent application, see:(i) Huang, W.-W.; Cheng, J.-T.; Hsiao, W.-T.; Chiou, W.-H. J. Org. Chem. 2024, 89, 5091. doi: 10.1021/acs.joc.3c02366 pmid: 22770123
	For the reaction of vinylogous amides, see:(j) Zhang, C. Y.; Lin, J. P.; Wang, L.; Mei, Y. X.; Wang, L. J.; Xie, Y. Q.; Lu, Y.; Tian, J. K.; Wang, W.; Chen, L. L.; Guo, M. P.; Zhou, C. L. J. Org. Chem. 2024, 89, 373. doi: 10.1021/acs.joc.3c02108 pmid: 22770123
[13]	For selected examples, see: (a) Heindl, S.; Riomet, M.; Matyasovsky, J.; Lemmerer, M.; Malzer, N.; Maulide, N. Angew. Chem. Int. Ed. 2021, 60, 19123. doi: 10.1002/anie.v60.35
	(b) Spieß, P.; Berger, M.; Kaiser, D.; Maulide, N. J. Am. Chem. Soc. 2021, 143, 10524. doi: 10.1021/jacs.1c04363
	(c) Li, J.; Berger, M.; Zawodny, W.; Simaan, M.; Maulide, N. Chem 2019, 5, 1883. doi: 10.1016/j.chempr.2019.05.006
[14]	(a) Kim, A. N.; Ngamnithiporn, A.; Du, E.; Stoltz, B. M. Chem. Rev. 2023, 123, 9447. doi: 10.1021/acs.chemrev.3c00054 pmid: 29324343
	(b) Chrzanowska, M.; Grajewska, A.; Rozwadowska, M. D. Chem. Rev. 2016, 116, 12369. pmid: 29324343
	(c) Capilla, A. S.; Soucek, R.; Grau, L.; Romero, M.; Rubio-Martínez, J.; Caignard, D. H.; Pujol, M. D. Eur. J. Med. Chem. 2018, 145, 51. doi: S0223-5234(17)31129-7 pmid: 29324343
[15]	(a) Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97. doi: 10.1021/ar9502341 pmid: 15250744
	(b) Uematsu, N.; Fujii, A.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 4916. doi: 10.1021/ja960364k pmid: 15250744
	(c) Lee, K. M.; Kim, J. C.; Kang, P.; Lee, W. K.; Eum, H.; Ha, H.-J. Tetrahedron 2012, 68, 883. doi: 10.1016/j.tet.2011.11.031 pmid: 15250744
	(d) Ružič, M.; Pečavar, A.; Prudič, D.; Kralj, D.; Scriban, C.; Zanotti-Gerosa, A. Org. Process Res. Dev. 2012, 16, 1293. doi: 10.1021/op3000543 pmid: 15250744
	(e) Chrzanowska, M.; Rozwadowska, M. D. Chem. Rev. 2004, 104, 3341. pmid: 15250744
	(f) Václavíková Vilhanová, B.; Budinská, A.; Václavík, J.; Matoušek, V.; Kuzma, M.; Červený, L. Eur. J. Org. Chem. 2017, 5131. pmid: 15250744
	(g) Balázsik, K.; Szőllősi, G.; Berkesi, O.; Szalontai, G.; Fülöp, F.; Bartók, M. Top. Catal. 2012, 55, 880. doi: 10.1007/s11244-012-9854-7 pmid: 15250744
	(h) Ding, Z.-Y.; Wang, T.; He, Y.-M.; Chen, F.; Zhou, H.-F.; Fan, Q.-H.; Guo, Q.; Chan, A. S. C. Adv. Synth. Catal. 2013, 355, 3727. doi: 10.1002/adsc.v355.18 pmid: 15250744
	(i) Ji, Y.; Gao, Q.; Han, W.; Fang, B. Catalysts 2024, 14, 884. doi: 10.3390/catal14120884 pmid: 15250744
[16]	(a) Szawkało, J.; Zawadzka, A.; Wojtasiewicz, K.; Leniewski, A.; Drabowicz, J.; Czarnocki, Z. Tetrahedron: Asymmetry 2005, 16, 3619. doi: 10.1016/j.tetasy.2005.10.007
	(b) Perez, M.; Wu, Z.; Scalone, M.; Ayad, T.; Ratovelomanana-Vidal, V. Eur. J. Org. Chem. 2015, 2015, 6503. doi: 10.1002/ejoc.v2015.29
	(c) Peng, P.; Zheng, Z.; Yu, J.; Gao, X.; Yang, J.; Zhao, C.; Zhang, F. Org. Process Res. Dev. 2022, 26, 3106. doi: 10.1021/acs.oprd.2c00243
[17]	He, Q.; Ye, J.-L.; Xu, F.-F.; Geng, H.; Chen, T.-T.; Chen, H.; Huang, P.-Q. J. Org. Chem. 2021, 86, 16300, and references cited therein.
[18]	(a) Ogo, S.; Abura, T.; Watanabe, Y. Organometallics 2002, 21, 2964. doi: 10.1021/om011059x pmid: 16268617
	(b) Rhyoo, H. Y.; Park, H.-J.; Suh, W. H.; Chung, Y. K. Tetrahedron Lett. 2002, 43, 269. pmid: 16268617
	(c) Wang, F.; Liu, H.; Cun, L.; Zhu, J.; Deng, J.; Jiang, Y. J. Org. Chem. 2005, 70, 9424. pmid: 16268617
	(d) Wu, X.; Li, X.; Hems, W.; King, F.; Xiao, J. Org. Biomol. Chem. 2004, 2, 1818. doi: 10.1039/b403627a pmid: 16268617
	(e) Li, C.; Xiao, J. J. Am. Chem. Soc. 2008, 130, 13208. doi: 10.1021/ja8050958 pmid: 16268617
	(f) Evanno, L.; Ormala, J.; Pihko, P. M. Chem.-Eur. J. 2009, 15, 12963. doi: 10.1002/chem.v15:47 pmid: 16268617
[19]	Bembenek, M. E.; Abell, C. W.; Chrisey, L. A.; Rozwadowska, M. D.; Gessner, W.; Brossi, A. J. Med. Chem. 1990, 33, 147. pmid: 2296014
[20]	Xu, C.-P.; Xiao, Z.-H.; Zhuo, B.-Q.; Wang, Y.-H.; Huang, P.-Q. Chem. Commun. 2010, 46, 7834. doi: 10.1039/c0cc01487g
[21]	Mujahidin, D.; Doye, S. Eur. J. Org. Chem. 2005, 2689.
[22]	Chuliá, S.; Ivorra, M. D.; Lugnier, C.; Vila, E.; Noguera, M. A.; D'Ocon, P. Br. J. Pharmacol. 1994, 113, 1377. doi: 10.1111/bph.1994.113.issue-4
[23]	Fodale, V.; Santamaria, L. B. Eur. J. Anaesthesiology 2002, 19, 466. doi: 10.1097/00003643-200207000-00002
[24]	(a) Li, W.; Jiang, M.; Chen, W.; Chen, Y.; Yang, Z.; Tang, P.; Chen, F. J. Org. Chem. 2021, 86, 8143. doi: 10.1021/acs.joc.1c00602 pmid: 21563765
	(b) Mastranzo, V. M.; Yuste, F.; Ortiz, B.; Sánchez-Obregón, R.; Toscano, R. A.; García Ruano, J. L. J. Org. Chem. 2011, 76, 5036. doi: 10.1021/jo2007237 pmid: 21563765
[25]	Steiner, M. A.; Gatfield, J.; Brisbare-Roch, C.; Dietrich, H.; Treiber, A.; Jenck, F.; Boss, C. ChemMedChem 2013, 8, 898. doi: 10.1002/cmdc.201300003 pmid: 23589487
[26]	(a) Ji, Y.; Wang, J.; Chen, M.; Shi, L.; Zhou, Y. Chin. J. Chem. 2018, 36, 139. doi: 10.1002/cjoc.v36.2
	(b) Gitto, R.; Ficarra, R.; Stancanelli, R.; Guardo, M.; De Luca, L.; Barreca, M. L.; Pagano, B.; Rotondo, A.; Bruno, G.; Russo, E.; De Sarro, G.; Chimirri, A. Bioorg. Med. Chem. 2007, 15, 5417. doi: 10.1016/j.bmc.2007.05.059
[27]	(a) Sakurai, T.; Amemiya, A.; Ishii, M.; Matsuzaki, I.; Chemelli, R. M.; Tanaka, H.; Williams, S. C.; Richardson, J. A.; Kozlowski, G. P.; Wilson, S.; Arch, J. R. S.; Buckingham, R. E.; Haynes, A. C.; Carr, S. A.; Annan, R. S.; McNulty, D. E.; Liu, W.-S.; Terrett, J. A.; Elshourbagy, N. A.; Bergsma, D. J.; Yanagisawa, M. Cell 1998, 92, 573. doi: 10.1016/s0092-8674(00)80949-6 pmid: 9491897
	(b) Reddy, N. S. S.; Reddy, B. V. S. Tetrahedron Lett. 2014, 55, 3157. doi: 10.1016/j.tetlet.2014.03.130 pmid: 9491897
[28]	(a) Leander, K.; Luning, B.; Ruusa, E. Acta Chem. Scand. 1969, 23, 244. doi: 10.3891/acta.chem.scand.23-0244
	(b) Brossi, A.; Teitel, S. Helv. Chim. Acta 1971, 54, 1564. doi: 10.1002/hlca.v54:6
[29]	Minor, D. L.; Wyrick, S. D.; Charifson, P. S.; Watts, V. J.; Nichols, D. E.; Mailman, R. B. J. Med. Chem. 1994, 37, 4317. pmid: 7996543
[30]	Zein, A. L.; Dakhil, O. O.; Dawe, L. N.; Georghiou, P. E. Tetrahedron Lett. 2010, 51, 177.

酰胺的“一瓶”催化不对称还原型Bischler-Napieralski反应: 生物活性1-取代四氢异喹啉的对映选择性合成