Dipeptides from Methionine and S-Methylcysteine as Chiral Ligands for Asymmetric Michael Reactions

Advanced Synthesis and Catalysis

Volumn 341, Issue 5, 1999, Pages 495-498

  Christoffers, Jens ^a  

^a TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

Author keywords

Asymmetric catalysis; Chirality; Michael additions; Peptides; Thioether ligands

Indexed keywords

EID: 0347155088     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3897(199907)341:5<495::aid-prac495>3.3.co;2-e     Document Type: Article

References (22)

1. a) M. S. Sigman, E. N. Jacobsen, J. Am. Chem. Soc. 1998, 120, 4901;
2. b) K. D. Shimizu, B. M. Cole, C. A. Krueger, K. W. Kuntz, M. L. Snapper, A. H. Hoveyda, Angew. Chem. 1997, 109, 1782; Angew. Chem. Int. Ed. Engl. 1997, 36, 1781;
3. b) K. D. Shimizu, B. M. Cole, C. A. Krueger, K. W. Kuntz, M. L. Snapper, A. H. Hoveyda, Angew. Chem. 1997, 109, 1782; Angew. Chem. Int. Ed. Engl. 1997, 36, 1781;
4. c) M. B. Francis, N. S. Finney, E. N. Jacobsen, J. Am. Chem. Soc. 1996, 188, 8983
5. a) J. Christoffers, Liebigs Ann./Recueil 1997, 1353;
6. b) J. Christoffers, U. Rößler, Tetrahedron: Asymmetry 1998, 9, 2349
7. a) K. Yamada, T. Arai, H. Sasai, M. Shibasaki, J. Org. Chem. 1998, 63, 3666;
8. b) Review: M. Shibasaki, H. Sasai, T. Arai, Angew. Chem. 1997, 109, 1290; Angew. Chem. Int. Ed. Engl. 1997, 36, 1236;
9. b) Review: M. Shibasaki, H. Sasai, T. Arai, Angew. Chem. 1997, 109, 1290; Angew. Chem. Int. Ed. Engl. 1997, 36, 1236;
10. c) N. End, L. Macko, M. Zehnder, A. Pfaltz, Chem. Eur. J. 1998, 4, 818;
11. d) Review: J. Leonard, E. Diez-Barra, S. Merino, Eur. J. Org. Chem. 1998, 2051
12. A. Q. Lyons, L. D. Pettit, J. Chem. Soc., Dalton Trans. 1984, 2305
13. M. Medal, Acta Chem. Scand. B 1986, B40, 250
14. J. Jiang, K. K. Schumacher, M. M. Joullie, F. A. Davis, R. E. Reddy, Tetrahedron Lett. 1994, 35, 2121
15. J. G. Wilson, L. A. Cohen, J. Am. Chem. Soc. 1963, 55, 560
16. E. Booth, V. C. E. Burnop. W. E. Jones, J. Chem. Soc. 1944, 666
17. The asymmetric synthesis of 5 was reported three times before: a) H. Wynberg, R. Helder, Tetrahedron Lett. 1975, 4057; b) Y. Tamai, A. Kamifuku, E. Koshiishi, S. Miyano, Chem. Lett. 1995, 957; c) H. Sasai, E. Emori, T. Arai, M. Shibasaki, Tetrahedron Lett. 1996, 37, 5561
18. The asymmetric synthesis of 5 was reported three times before: a) H. Wynberg, R. Helder, Tetrahedron Lett. 1975, 4057; b) Y. Tamai, A. Kamifuku, E. Koshiishi, S. Miyano, Chem. Lett. 1995, 957; c) H. Sasai, E. Emori, T. Arai, M. Shibasaki, Tetrahedron Lett. 1996, 37, 5561
19. The asymmetric synthesis of 5 was reported three times before: a) H. Wynberg, R. Helder, Tetrahedron Lett. 1975, 4057; b) Y. Tamai, A. Kamifuku, E. Koshiishi, S. Miyano, Chem. Lett. 1995, 957; c) H. Sasai, E. Emori, T. Arai, M. Shibasaki, Tetrahedron Lett. 1996, 37, 5561
20. For full spectral data of 5 see: J. Christoffers, J. Chem. Soc., Perkin Trans. 1 1997, 3141
21. J. Christoffers, A. Mann, U. Rößler, unpublished results
22. Review: J. Christoffers, Eur. J. Org. Chem. 1998, 1259