Catalytic enantioselective cross-Mannich reaction of aldehydes

Angewandte Chemie - International Edition

Volumn 45, Issue 3, 2006, Pages 348-352

  Marques, Maria Manuel B ^a  

^a UNIVERSIDADE NOVA DE LISBOA   (Portugal)

Author keywords

Asymmetric catalysis; C C coupling; Enantioselectivity; Homogeneous catalysis; Mannich reaction

Indexed keywords

AMINO ACIDS; CATALYSIS; CATALYST ACTIVITY;

ASYMMETRIC CATALYSIS; C-C COUPLING; ENANTIOSELECTIVITY; MANNICH REACTIONS;

ALDEHYDES;

ALDEHYDE;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SHORT SURVEY; STEREOISOMERISM; SYNTHESIS;

ALDEHYDES; CATALYSIS; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 30444441133     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200502630     Document Type: Short Survey

References (39)

1. Reviews: a) E. F. Kleinmann in Comprehensive Organic Synthesis, Vol. 2 (Ed.: B. M. Trost), Pergamon, New York, 1991, Chap. 4.1;
2. b) M. Arend, B. Westermann, N. Risch, Angew. Chem. 1998, 110, 1096;
3. Angew. Chem. Int. Ed. 1998, 37, 1044.
4. Review: S. Denmark, O. J.-C. Nicaise in Comprehensive Asymmetric Catalysis, Vol. 2 (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, p. 93.
5. Review: S. Kobayashi, H. Ishitani, Chem. Rev. 1999, 99, 1069, and references therein ;
6. for indirect methods employing stoichiometric amounts of chiral enol equivalents see: a) M. R. Naimi-Jamal, S. A. Webb, M. R. Saidi, J. Ipaktschi, Eur. J. Org. Chem. 1998, 197;
7. b) D. Enders, S. Oberbörsch, J. Adam, Synlett 2000, 644;
8. E. J. Corey, C. P. Cecicco, R. C. Newbold, Tetrahedron Lett. 1991, 32, 5287;
9. C. Palomo, M. Oiarbide, M. C. Gonzalez-Rego, A. K. Sharma, J. M. Garcia, A. Gonzalez, C. Landa, A. Linden, Angew. Chem. 2000, 112, 1105;
10. Angew. Chem. Int. Ed. 2000, 39, 1063.
11. a) S. Kobayashi, T. Hamada, K. Manabe, J. Am. Chem. Soc. 2002, 124, 5640;
12. b) S. Kobayashi, R. Matsubara, H. Kitagawa, Org. Lett. 2002, 4, 143;
13. c) Y. Hamashima, K. Yagi, H. Tamas, M. Sodeoka, J. Am. Chem. Soc. 2002, 124, 14530;
14. d) Y. Hamashima, M. Hotta, M. Sodeoka, J. Am. Chem. Soc. 2002, 124, 11240;
15. e) D. Ferraris, B. Young, C. Cox, T. Dudding, W. J. Drury III, L. Ryhkov, T. Taggi, T. Lectka, J. Am. Chem. Soc. 2002, 124, 67.
16. T. Hamda, K. Manabe, S. Kobayashi, J. Am. Chem. Soc. 2004, 126, 7768.
17. a) B. M. Trost, L. R. Terrell, J. Am. Chem. Soc. 2003, 125, 338;
18. b) S. Matsunaga, N. Kumagai, S. Harada, M. Shibasaki, J. Am. Chem. Soc. 2003, 125, 4712.
19. L. Bernardi, A. S. Gothelf, R. G. Hazell, K. A. Jørgensen, J. Org. Chem. 2003, 68, 2583.
20. A. Okada, T. Shibuguchi, T. Ohshima, H. Masu, K. Yamaguchi, M. Shibasaki, Angew. Chem. 2005, 117, 4640;
21. Angew. Chem. Int. Ed. 2005, 44, 4564.
22. a) "Asymmetric Synthesis of Optically Active Polycyclic Organic Compounds": Z. G. Hajos, D. R. Parrish, German patent DE 2102623, July 29, 1971;
23. b) "Optically Active 1,5-Indanone and 1,6-Naphthaledione": U. Eder, G. Sauer, R. Wiechert, German patent DE 2014757, Oct 7, 1971.
24. For a review on proline-catalyzed asymmetric reactions see: B. List, Tetrahedron 2002, 58, 5573.
25. a) B. List, J. Am. Chem. Soc. 2000, 122, 9336;
26. B. List, P. Pojarliev, W. T. Biller, H. Martin, J. Am. Chem. Soc. 2002, 124, 827;
27. b) W. Notz, K. Sakthievel, T. Bui, G. Zhong, C. F. Barbas III, Tetrahedron Lett. 2001, 42, 199;
28. S.-I. Watanabe, A. Córdova, F. Tanaka, C. F. Barbas III, Org. Lett. 2002, 4, 4519;
29. A. Córdova, W. Notz, G. Zhong, J. M. Betancort, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1842;
30. A. Córdova, C. F. Barbas III, Tetrahedron Lett. 2003, 44, 1923;
31. c) A. G. Wenzel, E. N. Jacobsen, J. Am. Chem. Soc. 2002, 124, 12964;
32. d) for a review of asymmetric aminocatalysis see: B. List, Synlett 2001, 1675.
33. A. Córdova, Synlett 2003, 1651.
34. A. Münch, B. Wendt, M. Christmann, Synlett 2004, 2751.
35. Y. Hayashi, W. Tsuboi, I. Ashimine, T. Urushima, M. Shoji, K. Sakai, Angew. Chem. 2003, 115, 3805;
36. Angew. Chem. Int. Ed. 2003, 42, 3677.
37. A. Córdova, Chem. Eur. J. 2004, 10, 1987.
38. A. J. A. Cobb, D. M. Shaw, D. A. Long-bottom, J. B. Gold, S. V. Ley, Org. Biomol. Chem. 2005, 3, 84.
39. A. Winter, N. Risch, Synthesis 2003, 2667.