Asymmetric alkynylation of imines by cooperative hydrogen bonding and metal catalysis

Angewandte Chemie - International Edition

Volumn 49, Issue 6, 2010, Pages 1013-1016

  De Armas, Pedro ^a,b   Tejedor, David ^a,b   García Tellado, Fernando ^a,b  

^a INSTITUTO DE PRODUCTOS NATURALES Y AGROBIOLOGÍA   (Spain)

^b Facultad de Ciencias Farmacéuticas y Bioquímicas   (Spain)

Author keywords

Asymmetric catalysis; Br nsted acids; Cooperative catalysis; Organocatalysis; Transition metals

Indexed keywords

ALKYNYLATIONS; ASYMMETRIC CATALYSIS; CATALYTIC CYCLES; COOPERATIVE CATALYSIS; H-BONDING; HYDROGEN BONDINGS; METAL CATALYSIS; ORGANOCATALYSIS; PROTECTING GROUP;

ACIDS; HYDROGEN BONDS; NITROGEN COMPOUNDS; RATE CONSTANTS; REACTION KINETICS; TRANSITION METALS;

CATALYSIS;

ALKENE; IMINE; METAL;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; HYDROGEN BOND; STEREOISOMERISM;

ALKENES; CATALYSIS; HYDROGEN BONDING; IMINES; METALS; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 76249109420     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.200906018     Document Type: Article

References (39)

1. a) For selected examples, see: J. J. Fleming, J. Du Bois, J. Am. Chem. Soc. 2006, 128, 3926-3927;
2. b) B. Jiang, M. Xu, Angew. Chem. 2004, 116, 2597-2600;
3. Angew. Chem. Int. Ed. 2004, 43, 2543-2546;
4. c)T. Yoon, M. D. Shair, S. J. Danishefsky, G.K. Shulte, J. Org. Chem. 1994, 59, 3752-3754, and references therein.
5. For selected examples, see: a) A. Hoepping, K.M. Johnson George, J. Flippen-Anderson, A. P. Kozikowski, J. Med. Chem. 2000, 43, 2064-2071;
6. b) N. Miyachi, F. Kanda, M. Shibasaki, J. Org. Chem. 1989, 54, 3511-3513;
7. c) M. Shibasaki, Y. Ishida, G. Iwasaki, T. Iimori, J. Org. Chem. 1987, 52, 33488-33489.
8. C. Swithenbank, P. J. McNulty, K. L. Viste, J. Agric. Food Chem. 1971, 19, 4417-4422.
9. a) J. L. Wright, T. F. Gregory, S. P. Kesten, P. A. Boxer, K. A. Serpa, L. T. Meltzer, L. D. Wise, S. A. Espitia, C. S. Konkoy, E. R. Whittemore, R. M. Woodward, J. Med. Chem. 2000, 43, 3408-3419;
10. b) P. H. Yu, B. Davis, A. A. Boulton, J. Med. Chem. 1992, 35, 3705-3713.
11. For selected reviews, see: a) B. M. Trost, A. H. Weissb, Adv. Synth. Catal. 2009, 351 ,963-983;
12. b) D. Tejedor, S. López-Tosco, F. Cruz-Acosta, G Méndez-Abt, F. García-Tellado, Angew. Chem. 2009, 121, 2124-2131;
13. Angew. Chem. Int. Ed. 2009, 48, 2090-2098.
14. For selected examples: a) M. Irmaka, M. M. K. Boysena, Adv. Synth. Catal. 2008, 350, 403-405;
15. b) Z. Shao, J. Wang, K. Ding, A. S. C. Chan, Adv. Synth. Catal. 2007, 349, 2375-2379;
16. c) T. F. Knöpfel, P. Aschwanden, T. Ichikawa, T. Watanabe, E. M. Carreira, Angew. Chem 2004, 116, 6097-6099;
17. Angew. Chem. Int. Ed 2004, 43, 5971-5973;
18. d) N. Gommermann, C. Koradin, K. Polborn, P. Knöchel, Angew. Chem. 2003, 115, 5941-5944;
19. Angew. Chem Int. Ed. 2003, 42, 5763-5766 ;
20. e) for seminal work in the enantioselective copper-catalyzed alkynylation of imines see: C. Wei, C.-J. Li, J. Am. Chem. Soc. 2002, 124, 5638-5639.
21. L. Zani, T. Eichhorn, C. Bolm, Chem. Eur. J. 2007, 13, 2587-2600.
22. J. F. Traverse, A. H. Hoveyda, M. L. Snapper, Org. Lett. 2003, 5, 3273-3275.
23. T. R. Wu, J. M. Chong, Org. Lett. 2006, 8, 15-18.
24. M. Rueping, A. P. Antonchick, C. Brinkmann, Angew. Chem. 2007, 119, 7027-7030;
25. Angew. Chem. Int. Ed 2007, 46, 6903-6906.
26. Y. Lu, T. C. Johnstone, B. A. Arndtsen, J. Am. Chem. Soc. 2009, 131, 11284-11285.
27. For a review, see: L. Zani, C. Bolm, Chem. Commun. 2006, 4263-4275.
28. For a review, see : T. Akiyama, J. Itoh, K. Fuchibe, Adv. Synth. Catal. 2006, 348, 999-1010.
29. Recent reviews: a)J.-K. Lee, M. C. Kung, H. H. Kung, Top. Catal. 2008, 49, 136-144;
30. b)J. C. Mareque Rivas, Curr. Org. Chem. 2007, 11, 1434-1449.
31. For selected recent examples, see: a) Z.-Y Han, H. Xiao, X.-H. Chen, L.-Z. Gong, J. Am. Chem. Soc. 2009, 131, 9182-9183;
32. b) W. Hu, X. Xu, J. Zhou, W.-J. Liu, H. Huang, J. Hu, L. Yang, L.Z. Gong, J. Am. Chem. Soc 2008, 130, 7782-7783;
33. c) S. Mukherjee, B. List, J. Am. Chem. Soc. 2007, 129, 11336-11337.
34. a) U. Halbes-Letinois, J. M. Weibel, P. Pale, Chem Soc. Rev. 2007, 36, 759-769;
35. b) whereas silver nitrate and triflate catalyze the alkynylation of α-imino esters in the absence of Brønsted acids, silver acetate results in low conversion even after prolonged reaction times. J.-X. Ji, T. T.-L. Au-Yeung, J. Wu, C.W. Yip, A. S. C. Chan, Adv. Synth. Catal. 2004, 546, 42-44;
36. c) the three component silver-catalyzed reaction of aldehydes, cyclic dialkylamines, and terminal alkynes has been described to occur in the absence of coactivators in water: C. Wei, Z. Li, C.-J. Li, Org. Lett. 2003, 5, 4473-4475.
37. For recent examples of this catalysis, see reference [15c] and G. L. Hamilton, E. J. Kang, M. Mba, F. D. Toste, Science 2007, 317, 496-499;
38. for a perspective article, see: J. Lacour, D. Linder, Science 2007, 577, 462-463.
39. Z. Shao, H. Zhan, Chem. Soc. Rev., 2009, 38, 2745-2755.