Enantioselective one-pot organocatalytic michael addition/goldcatalyzed tandem acetalization/cyclization

Angewandte Chemie - International Edition

Volumn 48, Issue 47, 2009, Pages 8923-8926

  Belot, Sébastien ^a   Vogt, Kim A ^b   Besnard, Céline ^a   Krause, Norbert ^b   Alexakis, Alexandre ^a  

^a UNIVERSITY OF GENEVA   (Switzerland)

^b TU DORTMUND UNIVERSITY   (Germany)

Author keywords

Cyclization; Gold; Heterocycles; Michael addition; Organocatalysis

Indexed keywords

DIASTEREO- AND ENANTIOSELECTIVITY; ENANTIOSELECTIVE; GOLD CATALYSIS; HETEROCYCLES; MICHAEL ADDITION; MICHAEL ADDITIONS; ONE POT; ONE POT PROCESS; ORGANOCATALYSIS; ORGANOCATALYTIC; TRIMETHYLSILYL;

ADDITION REACTIONS; CYCLIZATION; ENANTIOSELECTIVITY; ETHERS; GOLD; RATE CONSTANTS; REACTION KINETICS;

CATALYSIS;

EID: 70449095147     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200903905     Document Type: Article

References (42)

1. a) G. A. Olah, Angew. Chem. 2005, 117, 2692
2. Angew. Chem. Int. Ed. 2005, 44, 2636
3. b) N. Armaroli, V. Balzani, Angew. Chem. 2007, 119, 52
4. Angew. Chem. Int. Ed. 2007, 46, 52.
5. a) C. Bressy, P. I. Dalko, Enantioselective Organocatalysis, Wiley-VCH, Weinheim, 2007
6. b) Special issue on organocatalysis N°12, Chem. Rev. 2007, 107, 5413-5883.
7. Selected reviews on homogeneous gold catalysis: a) Z. Li, C. Brouwer, C. He, Chem. Rev. 2008, 108, 3239;
8. b) A. Arcadi, Chem. Rev. 2008, 108, 3266;
9. H. C. Shen, Tetrahedron 2008, 64, 3885;
10. A. Fürstner, P. W. Davis, Angew. Chem. 2007, 119, 3478;
11. Angew. Chem. Int. Ed. 2007, 46, 3410;
12. e) A. S. K. Hashmi, Chem. Rev. 2007, 107, 3180;
13. f) E. Jimenez-Nunez, A. M. Echavarren, Chem. Commun. 2007, 333;
14. g) A. Hoffmann-Röder, N. Krause, Org. Biomol. Chem. 2005, 3, 387.
15. C. J. Chapman, C. G. Frost, Synthesis 2007, 1.
16. X. Linghu, J. J. Kennedy-Smith, F. D. Toste, Angew. Chem. 2007, 119, 7815;
17. Angew. Chem. Int. Ed. 2007, 46, 7671.
18. a) S. Mukherjee, J. W. Yang, S. Hoffmann, B. List, Chem. Rev. 2007, 107, 5471 ;
19. b) S. B. Tsogoeva, Eur. J. Org. Chem. 2007, 1701;
20. D. Almasi, D. A. Alonso, C. Nájera, Tetrahedron: Asymmetry 2007, 18, 299;
21. S. Sulzer-Mossé, A. Alexakis, Chem. Commun. 2007, 3123;
22. e) A. Quintard, C. Bournaud, A. Alexakis, Chem. Eur. J. 2008, 14, 7504.
23. J. M. Betancort, K. Sakthivel, R. Thayumanavan, F. Tanaka, C. F. Barbas III, Synthesis 2004, 1509.
24. C. Palomo, S. Vera, A. Mielgo, E. Gomez-Bengoa, Angew. Chem. 2006, 118, 6130;
25. Angew. Chem. Int. Ed. 2006, 45, 5984.
26. D. Bonne, L. Salat, J.-P. Dulcère, J. Rodriguez, Org. Lett. 2008, 10, 5409.
27. a) E. Reyes, J. L. Vicario, D. Badía, L. Carillo, Org. Lett. 2006, 8, 6135;
28. b) S. Zhu, S. Yu, D. Ma, Angew. Chem. 2008, 120, 555;
29. Angew. Chem. Int. Ed. 2008, 47, 545.
30. a) O. Andrey, A. Vidonne, A. Alexakis, Tetrahedron Lett. 2003, 44, 7901;
31. b) R. Aslanian, G. Lee, R. V. Iyer, N.-Y. Shih, J. J. Piwinski, R. W. Draper, A. T. McPhail, Tetrahedron: Asymmetry 2000, 11, 3867.
32. a) L. Cui, Y. Peng, L. Zhang, J. Am. Chem. Soc. 2009, 131, 8394;
33. b) J. T. Binder, B. Crone, T. T. Haug, H. Menz, S. F. Kirsch, Org. Lett. 2008, 10, 1025;
34. Z. Shao, H. Zhang, Chem. Soc. Rev. 2009, 38, 2745.
35. S. Belot, A. Massaro, A. Tenti, A. Mordini, A. Alexakis, Org. Lett. 2008, 10, 4557.
36. a) V. Belting, N. Krause, Org. Lett. 2006, 8, 4489;
37. b) V. Belting, N. Krause, Org. Biomol. Chem. 2009, 7, 1221;
38. for a related tandem reaction, see: T. Godet, C. Vaxelaire, C. Michel, A. Millet, P. Belmont, Chem. Eur. J. 2007, 13, 5632.
39. CCDC 737010 (4i) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www. ccdc.cam.ac.uk/data-request/cif.
40. See for example: a) M. Uemura, I. D. G. Watson, M. Katsukawa, F. D. Toste, J. Am. Chem. Soc. 2009, 131, 3464;
41. b) C.-M. Chao, M. R. Vitale, P. Y. Toullec, J.-P. Genêt, V. Michelet, Chem. Eur. J. 2009, 15, 1319;
42. G. L. Hamilton, E. J. Kang, M. Mba, F. D. Toste, Science 2007, 317, 496.