Highly stereoselective allylic alkylations of peptides

Angewandte Chemie - International Edition

Volumn 45, Issue 29, 2006, Pages 4855-4858

  Kazmaier, Uli ^a   Deska, Jan ^a   Watzke, Anja ^a  

^a SAARLAND UNIVERSITY   (Germany)

Author keywords

Allylation; Asymmetric synthesis; Chelates; Palladium; Peptides

Indexed keywords

ALLYLATION; CHELATES; KWD ASYMMETRIC SYNTHESIS;

ALKYLATION; PALLADIUM; POLYMERS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

POLYPEPTIDES;

PALLADIUM; PEPTIDE;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALKYLATION; CATALYSIS; MOLECULAR STRUCTURE; PALLADIUM; PEPTIDES; STEREOISOMERISM;

EID: 33746813569     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200600509     Document Type: Article

References (40)

1. Reviews: a) M. A. Marahiel, T. Stachelhaus, H. D. Moetz, Chem. Rev. 1997, 97, 2651-2673;
2. b) H. v. Döhren, U. Keller, J. Vater, R. Zocher, Chem. Rev. 1997, 97, 2675-2705.
3. Reviews: a) D. R. W. Hogson, J. M. Sanderson, Chem. Soc. Rev. 2004, 33, 422-430;
4. b) N. Fusetani, S. Matsunaga, Chem. Rev. 1993, 93, 1793-1806.
5. a) A. D. Hess, A. Esa, P. M. Colombani, Transplant. Proc. 1988, 20, 29-40;
6. b) H. Fliri, in Antibiotics and Antiviral Compounds (Eds.: K. Krohn, H. A. Kirst, H. Maag), VCH, Weinheim, 1993, pp. 229-240.
7. a) J.-C. Gfeller, A. K. Beck, D. Seebach, Helv. Chim. Acta 1980, 63, 728-732;
8. b) M. J. Dunn, S. Gomez, R. F. W. Jackson, J. Chem. Soc. Perkin Trans. 1 1995, 1639-1640;
9. c) J. Barluenga, M. A. García-Martín; J. M. González, P. Clapés, G. Valencia, Chem. Commun. 1996, 1505-1506.
10. a) C. J. Easton, I. M. Scharfbillig, E. W. Tan, Tetrahedron Lett. 1988, 29, 1565-1568;
11. b) G. Apitz, W. Steglich, Tetrahedron Lett. 1991, 32, 3163-3166;
12. c) W. Steglich, M. Jäger, S. Jaroch, P. Zistler, Pure Appl. Chem. 1994, 66, 2167-2170.
13. a) M. Ricci, P. Blakskjaer, T. Skrydstrup, J. Am. Chem. Soc. 200, 122, 12 413-12 421;
14. b) M. Ricci, L. Madariaga, T. Skrydstrup, Angew. Chem. 2000, 112, 248-252;
15. Angew. Chem. Int. Ed. 2000, 39, 2242-2246;
16. c) C. J. Easton, Chem. Rev. 1997, 97, 53-82.
17. Reviews: a) D. Seebach, Angew. Chem. 1988, 100, 1685-1715;
18. Angew. Chem. Int. Ed. Engl. 1988, 27, 1624-1654;
19. b) D. Seebach, Aldrichimica Acta 1992, 25, 59-66;
20. c) D. Seebach, A. K. Beck, A. Studer in Modern Synthetic Methods, Vol. 7 (Eds.: B. Ernst, C. Leumann), Helvetica Chimica Acta/VCH, Basel/Weinheim, 1995, pp. 1-178.
21. a) D. Seebach, A. K. Beck, H. G. Bossler, C. Gerber, S. Y. Ko, C. W. Murtiashaw, R. Naef, S.-I. Shoda, A. Thaler, M. Krieger, R. Wenger, Helv. Chim. Acta 1993, 76, 1564-1590;
22. b) S. A. Miller, S. L. Griffiths, D. Seebach, Helv. Chim. Acta 1993, 76, 563-595.
23. a) U. Kazmaier, J. Org. Chem. 1994, 59, 6667-6670;
24. b) U. Kazmaier, S. Maier, Chem. Commun. 1998, 2535-2536;
25. c) U. Kazmaier, S. Maier, Org. Lett. 1999, 1, 1763-1766;
26. d) U. Kazmaier, S. Maier, F. L. Zumpe, Synlett 2000, 1523-1535;
27. e) S. Maier, U. Kazmaier, Eur. J. Org. Chem. 2000, 1241-1251.
28. U. Kazmaier, S. Maier, J. Org. Chem. 1999, 64, 4574-4575.
29. Review on peptide-metal complexes: K. Severin, R. Bergs, W. Beck, Angew. Chem. 1998, 110, 1722-1743;
30. Angew. Chem. Int. Ed. 1998, 57, 1634-1654.
31. a) U. Kazmaier, F. L. Zumpe, Angew. Chem. 1999, 111, 1572-1574;
32. Angew. Chem. Int. Ed. 1999, 38, 1468-1470;
33. b) U. Kazmaier, F. L. Zumpe, Angew. Chem. 2000, 112, 805-807;
34. Angew. Chem. Int. Ed. 2000, 39, 802-804;
35. c) T. D. Weiß, G. Helmchen, U. Kazmaier, Chem. Commun. 2002, 1270-1271;
36. d) U. Kazmaier, Curr. Org. Chem. 2003, 317-328;
37. e) U. Kazmaier, M. Pohlman, Synlett 2004, 623-626;
38. f) U. Kazmaier, T. Lindner, Angew. Chem. 2005, 117, 3368-3371;
39. Angew. Chem. Int. Ed. 2005, 44, 3303-3306.
40. major = 19.62 min.