An easy route to exotic 9-epimers of 9-amino-(9-deoxy) cinchona alkaloids with (8S, 9R) and (8R, 9S)-configurations through two inversions of configuration

Chinese Chemical Letters

Volumn 25, Issue 4, 2014, Pages 557-560

  Wan, Jing Wei ^a   Ma, Xue Bing ^a   He, Rong Xing ^a   Li, Ming ^a  

^a SOUTHWEST UNIVERSITY   (China)

Author keywords

9 Amino (9 deoxy) cinchona alkaloids; Cinchona alkaloids; Inversion of configuration; Synthesis

Indexed keywords

EID: 84898541845     PISSN: 10018417     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cclet.2013.12.008     Document Type: Article

References (33)

1. J. Seayad, and B. List Asymmetric organocatalysis Org. Biomol. Chem. 3 2005 719 724
2. C.F. Barbas III Organocatalysis lost: modern chemistry, ancient chemistry, and an unseen biosynthetic apparatus Angew. Chem. Int. Ed. 47 2008 42 47
3. W. Notz, F. Tanaka, and C.F. Barbas III Enamine-based organocatalysis with proline and diamines: the development of direct catalytic asymmetric Aldol, Mannich, Michael, and Diels-Alder reactions Acc. Chem. Res. 37 2004 580 591
4. H. Chen, R. Jiang, and Q.F. Wang et al. Synthesis of chiral dihydrofuran compounds by thiourea derivatives-catalyzed "interrupted" Feist-Bénary reaction Chin. Chem. Lett. 21 2010 167 170
5. S.K. Tian, Y.G. Chen, and J.F. Hang et al. Asymmetric organic catalysis with modified cinchona alkaloids Acc. Chem. Res. 37 2004 621 631
6. S.J. Connon Asymmetric catalysis with bifunctional cinchona alkaloid-based urea and thiourea organocatalysts Chem. Commun. 2008 2499 2510
7. T. Marcelli, and H. Hiemstra Cinchona alkaloids in asymmetric organocatalysis Synthesis 8 2010 1229 1279
8. J. Zhou, V. Wakchaure, P. Kraft, and B. List Primary-amine-catalyzed enantioselective intramolecular aldolizations Angew. Chem. Int. Ed. 47 2008 7656 7658
9. B.L. Zheng, Q.Z. Liu, C.S. Guo, X.L. Wang, and L. He Highly enantioselective direct Aldol reaction catalyzed by cinchona derived primary amines Org. Biomol. Chem. 5 2007 2913 2915
10. J.Q. Zhou, J.W. Wan, X.B. Ma, and W. Wang Copolymer-supported heterogeneous organocatalyst for asymmetric Aldol addition in aqueous medium Org. Biomol. Chem. 10 2012 4179 4185
11. W. Wang, X.B. Ma, J.W. Wan, J. Cao, and Q. Tang Preparation and confinement effect of a heterogeneous 9-amino-9-deoxy-epi-cinchonidine organocatalyst for asymmetric Aldol addition in aqueous medium Dalton Trans. 41 2012 5715 5726
12. R.P. Singh, K. Bartelson, and Y. Wang et al. Enantioselective Diels-Alder reaction of simple α,β-unsaturated ketones with a cinchona alkaloid catalyst J. Am. Chem. Soc. 130 2008 2422 2423
13. H.M. Li, Y.Q. Wang, and L. Deng Enantioselective Friedel-Crafts reaction of indoles with carbonyl compounds catalyzed by bifunctional cinchona alkaloids Org. Lett. 8 2006 4063 4065
14. G. Bartoli, M. Bosco, and A. Carlone et al. Organocatalytic asymmetric Friedel-Crafts alkylation of indoles with simple α,β-unsaturated ketones Org. Lett. 9 2007 1403 1405
15. P. Hammar, T. Marcelli, H. Hiemstra, and F. Himo Density functional theory study of the Cinchona thiourea-catalyzed Henry reaction: mechanism and enantioselectivity Adv. Synth. Catal. 349 2007 2537 2548
16. T.Y. Liu, H.L. Cui, and J. Long et al. Organocatalytic and highly stereoselective direct vinylogous Mannich reaction J. Am. Chem. Soc. 129 2007 1878 1879
17. P.F. Li, Y.C. Wang, X.M. Liang, and J.X. Ye Asymmetric multifunctional organocatalytic Michael addition of nitroalkanes to α,β-unsaturated ketones Chem. Commun. 28 2008 3302 3304
18. B. Vakulya, S. Varga, A. Csámpai, and T. Soós Highly enantioselective conjugate addition of nitromethane to chalcones using bifunctional cinchona organocatalysts Org. Lett. 7 2005 1967 1969
19. J.P. Malerich, K. Hagihara, and V.H. Rawal Chiral squaramide derivatives are excellent hydrogen bond donor catalysts J. Am. Chem. Soc. 130 2008 14416 14417
20. H.Y. Jiang, C.F. Yang, and C. Li et al. Heterogeneous enantioselective hydrogenation of aromatic ketones catalyzed by cinchona- and phosphine-modified iridium catalysts J. Angew. Chem. Int. Ed. 47 2008 9240 9244
21. X.W. Wang, C.M. Reisinger, and B. List Catalytic asymmetric epoxidation of cyclic enones J. Am. Chem. Soc. 130 2008 6070 6071
22. X.J. Lu, Y. Liu, B.F. Sun, B. Cindric, and L. Deng Catalytic enantioselective peroxidation of α,β-unsaturated ketones J. Am. Chem. Soc. 130 2008 8134 8135
23. Q.F. Wang, H. Chen, and P. Liu et al. Asymmetric epoxidation of alpha, beta-enones catalyzed by chiral amine salts Chin. J. Org. Chem. 29 2009 1617 1620
24. X.D. Liu, X.L. Bai, X.P. Qiu, and L.X. Gao Asymmetric phase-transfer mediated epoxidation of alpha, beta-enones using dendritic catalysts derived from cinchona alkaloids Chin. Chem. Lett. 16 2005 975 978
25. W. Chen, W. Du, and Y.Z. Duan et al. Enantioselective 1,3-dipolar cycloaddition of cyclic enones catalyzed by multifunctional primary amines: beneficial effects of hydrogen bonding Angew. Chem. Int. Ed. 46 2007 7667 7670
26. H. Brunner, and M.A. Baur α-Amino acid derivatives by enantioselective decarboxylation Eur. J. Org. Chem. 2003 2854 2862
27. S.H. Oh, H.S. Rho, and J.W. Lee et al. A highly reactive and enantioselective bifunctional organocatalyst for the methanolytic desymmetrization of cyclic anhydrides: prevention of catalyst aggregation Angew. Chem. Int. Ed. 47 2008 7872 7875
28. H.S. Rho, S.H. Oh, and J.W. Lee et al. Bifunctional organocatalyst for methanolytic desymmetrization of cyclic anhydrides: increasing enantioselectivity by catalyst dilution Chem. Commun. 2008 1208 1210
29. M. Bartók Unexpected inversions in asymmetric reactions: reactions with chiral metal complexes, chiral organocatalysts, and heterogeneous chiral catalysts Chem. Rev. 110 2010 1663 1705
30. Ł. Sidorowicz, and J. Skarżewski Easy access to 9-epimers of cinchona alkaloids: one-pot inversion by Mitsunobu esterification-saponification Synthesis 5 2011 708 710
31. H. Brunner, J. Bügler, and B. Nuber Enantioselective catalysis 98. Preparation of 9-amino(9-deoxy)cinchona alkaloids Tetrahedron: Asymmetry 6 1995 1699 1702
32. C.G. Oliva, A.M.S. Silva, D.I.S.P. Resende, F.A.A. Paz, and J.A.S. Cavaleiro Highly enantioselective 1,4-Michael additions of nucleophiles to unsaturated aryl ketones with organocatalysis by bifunctional cinchona alkaloids Eur. J. Org. Chem. 2010 3449 3458
33. H. Brunner, P. Schmidt, and M. Prommesberger Enantioselective catalysis. Part 133: Conformational analysis of amides of 9-amino(9-deoxy)epicinchonine Tetrahedron: Asymmetry 11 2000 1501 1502