Catalysis of highly stereoselective Mannich-type reactions of ketones with α-imino esters by a pyrrolidine-sulfonamide. Synthesis of unnatural α-amino acids

Tetrahedron Letters

Volumn 45, Issue 39, 2004, Pages 7243-7246

  Wang, Wei ^a   Wang, Jian ^a   Li, Hao ^a  

^a UNIVERSITY OF NEW MEXICO   (United States)

Author keywords

Amino acids; Asymmetric catalysis; Ketones; Mannich reaction; Pyrrolidine sulfonamide

Indexed keywords

AMINO ACID DERIVATIVE; ESTER DERIVATIVE; KETONE DERIVATIVE; PYRROLIDINE DERIVATIVE; SULFONAMIDE;

ARTICLE; CATALYSIS; CATALYST; DIASTEREOISOMER; ENANTIOSELECTIVITY; MANNICH REACTION; STEREOCHEMISTRY;

EID: 4444276557     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.08.032     Document Type: Article

References (37)

1. Reviews on synthesis of α-amino acids, see: R.M. Williams Synthesis of Optically Active α-Amino Acids 1989 Pergamon Oxford
2. R.M. Williams Advances in Asymmetric Synthesis 1 1995 45 94
3. R.O. Duthaler Tetrahedron 50 1994 1539 1650
4. S. Hanessian, G. McNaughton-Smith, H.-G. Lombart, and W.D. Lubell Tetrahedron 53 1997 12789
5. S. Kotha Acc. Chem. Res. 36 2003 342
6. K. Maruoka, and T. Ooi Chem. Rev. 103 2003 3013 3028
7. Reviews on the Mannich reactions, see: S.E. Denmark, and O.J.-C. Nicaise E.N. Jacobsen A. Pfaltz H. Yamamoto Comprehensive Asymmetric Catalysis 1999 Springer Heidelberg p 926
8. D. Arend, B. Westermann, and N. Risch Angew. Chem., Int. Ed. 37 1998 1044 1070
9. Excellent reviews on recent development of the Mannich-type of reactions of carbonyl compounds with α-imino esters: A.E. Taggi, A.M. Hafez, and T. Lectka Acc. Chem. Res. 36 2003 10 19
10. A. Córdova Acc. Chem. Res. 37 2004 102 122
11. H. Ishitani, M. Ueno, and S. Kobayashi J. Am. Chem. Soc. 119 1997 7153 7154
12. S. Kobayashi, T. Hamada, and K. Manabe J. Am. Chem. Soc. 124 2002 5640 5641
13. H. Ishitani, S. Ueno, and S. Kobayashi J. Am. Chem. Soc. 122 2000 8180 8186
14. E. Hagiwara, A. Fujii, and M. Sodeoka J. Am. Chem. Soc. 120 1998 2474 2475
15. A. Fujii, E. Hagiwara, and M. Sodeoka J. Am. Chem. Soc. 121 1999 545 556
16. D. Ferraris, B. Young, T. Dudding, and T. Lectka J. Am. Chem. Soc. 120 1998 2474 2475
17. D. Ferraris, B. Young, C. Cox, T. Dudding, W.J. Drury III, L. Ryzhkov, T. Taggi, and T. Lectka J. Am. Chem. Soc. 124 2002 67 77
18. S. Yamasaki, T. Iida, and M. Shibasaki Tetrahedron Lett. 40 1999 307 310
19. B.M. Trost, and L.M. Terrell J. Am. Chem. Soc. 125 2003 338 339
20. K. Juhl, N. Gathergood, and K.A. Jorgensen Angew. Chem., Int. Ed. 40 2001 2995 2997
21. Excellent reviews on organocatalysts: a general review, see: P.I. Dalko, and L. Moisan Angew. Chem., Int. Ed. 40 2001 3726 3748
22. A review of proline-catalyzed reactions, see: B. List Tetrahedron 58 2002 5573 5590
23. B. List, R.A. Lerner, and C.F. Barbas III J. Am. Chem. Soc. 122 2000 2395 2396
24. K.A. Ahrendt, C.J. Borths, and D.W.C. MacMillan J. Am. Chem. Soc. 122 2000 4243 4244
25. l-Proline-catalyzed the direct three component Mannich reactions, see: B. List J. Am. Chem. Soc. 122 2000 9336 9337
26. B. List, P. Pojarliev, W.T. Biller, and H.J. Martin J. Am. Chem. Soc. 124 2002 827 833
27. Y. Hayashi, W. Tsuboi, M. Shoji, and N. Suzuki J. Am. Chem. Soc. 125 2003 11208 11209
28. Y. Hayashi, W. Tsuboi, I. Ashimine, T. Urushima, M. Shoji, and K. Sakai Angew. Chem., Int. Ed. 42 2003 3677 3680
29. l-Proline-catalyzed the direct Mannich-type reactions of ketones and aldehydes with α-imino esters, see: A. Córdova, W. Notz, G. Zhong, J.M. Betancort, and C.F. Barbas III J. Am. Chem. Soc. 124 2002 1842 1843
30. A. Córdova, S. Watanabe, F. Tanaka, W. Notz, and C.F. Barbas III J. Am. Chem. Soc. 124 2002 1866 1867
31. A. Córdova, and C.F. Barbas III Tetrahedron Lett. 44 2003 1923 1926
32. Thiourea peptides catalyzed the Mannich-type reactions, see: P. Vachal, and E.N. Jacobsen J. Am. Chem. Soc. 124 2002 10012 10013
33. A.G. Wenzel, and E.N. Jacobsen J. Am. Chem. Soc. 124 2002 12964 12965
34. Pyrrolidine tetrazole catalyzed the Mannich-type reactions, see: A.J.A. Cobb, D.M. Shaw, and S.V. Ley Synlett 2004 558 560
35. Phosphoric acids catalyzed the Mannich-type reactions, see: T. Akiyama, J. Itoh, K. Yokota, and K. Fuchibe Angew. Chem., Int. Ed. 43 2004 1566 1568
36. D. Uraguchi, and M. Terada J. Am. Chem. Soc. 126 2004 5356 5357
37. Wang, W.; Wang, J.; Li, H. Tetrahedron Lett., accepted for publication