New chiral auxiliaries for the construction of quaternary stereocenters by copper-catalyzed Michael reactions

Angewandte Chemie - International Edition

Volumn 39, Issue 15, 2000, Pages 2752-2754

  Christoffers, Jens ^a   Mann, Alexander ^a  

^a TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

Author keywords

Amino acids; Asymmetric catalysis; Combinatorial chemistry; Copper; Michael additions

Indexed keywords

AMIDE; AMINO ACID; COPPER;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034604627     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20000804)39:15<2752::AID-ANIE2752>3.0.CO;2-5     Document Type: Article

References (32)

1. Reviews: a) E. J. Corey, A. Guzman-Perez, Angew. Chem. 1998, 110, 402-415; Angew. Chem. Int. Ed. 1998, 37, 388-401; b) K. Fuji, Chem. Rev. 1993, 93, 2037-2066.
2. Reviews: a) E. J. Corey, A. Guzman-Perez, Angew. Chem. 1998, 110, 402-415; Angew. Chem. Int. Ed. 1998, 37, 388-401; b) K. Fuji, Chem. Rev. 1993, 93, 2037-2066.
3. Reviews: a) E. J. Corey, A. Guzman-Perez, Angew. Chem. 1998, 110, 402-415; Angew. Chem. Int. Ed. 1998, 37, 388-401; b) K. Fuji, Chem. Rev. 1993, 93, 2037-2066.
4. Reviews: a) E. D. Bergmann, D. Ginsburg, R. Pappo, Org. React. 1959, 10, 179-555; b) D. A. Oare, C. H. Heathcock in Topics in Stereochemistry, Vol. 19 (Eds.: E. L. Eliel, S. H. Wilen), Wiley Interscience, New York, 1989, pp. 227-407; c) P. Perlmutter, Conjugate Addition Reactions in Organic Synthesis, Tetrahedron Organic Chemistry Series Vol. 9, Pergamon, Oxford, 1992.
5. Reviews: a) E. D. Bergmann, D. Ginsburg, R. Pappo, Org. React. 1959, 10, 179-555; b) D. A. Oare, C. H. Heathcock in Topics in Stereochemistry, Vol. 19 (Eds.: E. L. Eliel, S. H. Wilen), Wiley Interscience, New York, 1989, pp. 227-407; c) P. Perlmutter, Conjugate Addition Reactions in Organic Synthesis, Tetrahedron Organic Chemistry Series Vol. 9, Pergamon, Oxford, 1992.
6. Reviews: a) E. D. Bergmann, D. Ginsburg, R. Pappo, Org. React. 1959, 10, 179-555; b) D. A. Oare, C. H. Heathcock in Topics in Stereochemistry, Vol. 19 (Eds.: E. L. Eliel, S. H. Wilen), Wiley Interscience, New York, 1989, pp. 227-407; c) P. Perlmutter, Conjugate Addition Reactions in Organic Synthesis, Tetrahedron Organic Chemistry Series Vol. 9, Pergamon, Oxford, 1992.
7. a) J. Christoffers, J. Chem. Soc. Perkin Trans, 1 1997, 3141-3149;
8. b) review: J. Christoffers, Eur. J. Org. Chem. 1998, 1259-1266.
9. a) H. Brunner, B. Hammer, Angew. Chem. 1984, 96, 305-306; Angew. Chem. Int. Ed. Eng. 1984, 23, 312-313;
10. a) H. Brunner, B. Hammer, Angew. Chem. 1984, 96, 305-306; Angew. Chem. Int. Ed. Eng. 1984, 23, 312-313;
11. b) G. Desimoni, G. Dusi, G. Faita, P. Quadrelli, P. Righetti, Tetrahedron 1995, 51, 4131-4144;
12. c) N. End, L. Macko, M. Zehnder, A. Pfaltz, Chem. Eur. J. 1998, 4, 818-824.
13. a) H. Sasai, T. Arai, Y. Satow, K. N. Houk, M. Shibasaki, J. Am. Chem. Soc. 1995, 117, 6194-6198;
14. b) review: M. Shibasaki, H. Sasai, T. Arai, Angew. Chem. 1997, 109, 1290-1310; Angew. Chem. Int. Ed. Eng. 1997, 36, 1236-1256.
15. b) review: M. Shibasaki, H. Sasai, T. Arai, Angew. Chem. 1997, 109, 1290-1310; Angew. Chem. Int. Ed. Eng. 1997, 36, 1236-1256.
16. a) M. Pfau, G. Revial, A. Guingant, J. d'Angelo, J. Am. Chem. Soc. 1985, 107, 273-274;
17. reviews: b) J. d'Angelo, D. Desmaële, F. Dumas, A. Guingant, Tetrahedron: Asymmetry 1992, 3, 459-505;
18. c) J. Leonard, E. Diez-Barra, S. Merino, Eur. J. Org. Chem. 1998, 2051-2061.
19. A. Guingant, H. Hammami, Tetrahedron: Asymmetry 1991, 2, 411-414.
20. J. Christoffers, U. Rößler, T. Werner, Eur. J. Org. Chem. 2000, 701-705.
21. H. Sasai, E. Emori, T. Arai, M. Shibasaki, Tetrahedron Lett. 1996, 37, 5561-5564.
22. a) K. Tomioka, W. Seo, K. Ando, K. Koga, Tetrahedron Lett. 1987, 28, 6637-6640;
23. b) K. Ando, W. Seo, K. Tomioka, K. Koga, Tetrahedron 1994, 50, 13081-13088.
24. a) J. Christoffers, A. Mann, J. Pickardt, Tetrahedron 1999, 55, 5377-5388;
25. b) J. Christoffers, A. Mann, Eur. J. Org. Chem. 1999, 1475-1479;
26. c) J. Christoffers, J. Prakt. Chem. 1999, 341, 495-498;
27. d) J. Christoffers. U. Rößler, Tetrahedron: Asymmetry 1999, 10, 1207-1215.
28. 2, 90-99%. Boc = tert-butoxycarbonyl, DMAP = 4-dimethylaminopyridine, DCC = dicyclohexylcarbodiimide.
29. 2.
30. 2.
31. Details about GC analysis and derivatization procedures have recently been reported by us. [8]
32. Auxiliary 2 can be almost quantitatively recovered from the aqueous layer after basic workup.