Catalysis with phosphine-containing amino acids in various "turn" motifs

Journal of Organic Chemistry

Volumn 69, Issue 23, 2004, Pages 8077-8085

  Agarkov, Anton ^a   Greenfield, Scott J ^a   Ohishi, Takahiro ^a   Collibee, Scott E ^a   Gilbertson, Scott R ^b  

^a WASHINGTON UNIVERSITY   (United States)

^b University of Texas Medical Branch School of Medicine   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; CATALYSIS; POLYPEPTIDES;

LIGANDS; PEPTIDES; PHOSPHINE;

AMINO ACIDS;

AMINO ACID; CYCLOPENTENE DERIVATIVE; CYCLOPENTENYL ACETATE; DIMETHYLMALONATE; LIGAND; MALONIC ACID DERIVATIVE; PALLADIUM; PHOSPHINE DERIVATIVE; PROLINE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ALLYLATION; AMINO ACID SEQUENCE; ARTICLE; CATALYSIS; ENANTIOSELECTIVITY; PROTEIN MOTIF; PROTEIN STRUCTURE; REACTION ANALYSIS; SYNTHESIS;

AMINO ACID SEQUENCE; AMINO ACIDS; CATALYSIS; LIGANDS; MODELS, MOLECULAR; OLIGOPEPTIDES; PHOSPHINES; PROTEIN STRUCTURE, SECONDARY; STEREOISOMERISM;

EID: 8644232516     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049103g     Document Type: Article

References (30)

1. Gilbertson, S. R.; Chen, G.; McLoughlin, M. J. Am. Chem. Soc. 1994, 116, 4481-4482.
2. Gilbertson, S. R.; Wang, X. J. Org. Chem. 1996, 61, 434-435.
3. Gilbertson, S. R.; Wang, X. Tetrahedron Lett. 1996, 37, 6475-6478.
4. Gilbertson, S. R.; Wang, X. Tetrahedron 1999, 11609-11619.
5. Gilbertson, S. R.; Collibee, S. E.; Agarkov, A. J. Am. Chem. Soc. 2000, 122, 6522-6523.
6. Gilbertson, S. R. In Progress in Inorganic Chemistry; Karlen, K. D., Ed.; John Wiley & Sons: New York, 2001; Vol. 50, pp 433-471.
7. Greenfield, S. J.; Gilbertson, S. R. Synthesis 2001, 2337-2340.
8. Greenfield, S. J.; Agarkov, A.; Gilbertson, S. R. Org. Lett. 2003, 5, 3069-3072.
9. Miller, S. J.; Copeland, G. T.; Papaioannou, N.; Horstmann, T. E.; Ruel, E. M. J. Am. Chem. Soc. 1998, 120, 1629.
10. Sculimbrene, B., R.; Miller, S. J. J. Am. Chem. Soc. 2001, 123, 10125-10126.
11. Guerin, D. J.; Miller, S. J. J. Am. Chem. Soc. 2002, 124, 2134-2136.
12. Sculimbrene, B., R.; Morgan, A., J.; Miller, S. J. J. Am. Chem. Soc. 2002, 124.
13. Imperiali, B.; Kapoor, T. M. Tetrahedron 1993, 49, 3501-3510.
14. Imperiali, B.; Fisher, S. L.; Moats, R. A.; Prins, T. J. J. Am. Chem. Soc. 1992, 114, 3182-3188.
15. Haque, T. S.; Little, J. C.; Gellman, S. H. J. Am. Chem. Soc. 1994, 116, 4105-4106.
16. Haque, T. S.; Little, J. C.; Gellman, S. H. J. Am. Chem. Soc. 1996, 118, 6975-6985.
17. Chung, Y. J.; Christianson, L. A.; Stanger, H. E.; Powell, D. R.; Gellman, S. H. J. Am. Chem. Soc. 1998, 120, 10555-10556.
18. Huck, B. R.; Fisk, J. D.; Guzei, I. A.; Carlson, H. A.; Gellman, S. H. J. Am. Chem. Soc. 2003, 125, 9035-9037.
19. Huck, B. R.; Fisk, J. D.; Gellman, S. H. Org. Lett. 2000, 2, 2607-2610.
20. Arnold, U.; Hinderaker, M. P.; Nilsson, B. L.; Huck, B. R.; Gellman, S. H.; Raines, R. T. J. Am. Chem. Soc. 2002, 124, 8522-8523.
21. Chung, Y. J.; Huck, B. R.; Christianson, L. A.; Stanger, H. E.; Krauthauser, S.; Powell, D. R.; Gillman, S. H. J. Am. Chem. Soc. 2000, 122, 3995-4004.
22. Lai, J. R.; Huck, B. R.; Weisblum, B.; Gellman, S. H. Biochemistry 2002, 41, 12835-12842.
23. Evans, D. A.; Campos, K. R.; Tedrow, J. S.; Michael, F. E.; Gagne, M. R. J. Am. Chem. Soc. 2000, 122, 7905-7920.
24. Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1984, 116, 4089.
25. Trost, B. M.; Bunt, R. C. Angew. Chem., Int. Ed. Engl. 1996, 35, 99-102.
26. Trost, B. M. In Catalytic Asymmetric Synthesis; Ojima, T., Ed.; Wiley-VCH: New York, 2000; p 593.
27. Uozumi, Y.; Shibatomi, K. J. Am. Chem. Soc. 2001, 123, 2919-2920.
28. Kudis, S.; Helmchen, G. Angew. Chem., Int. Ed. 1998, 37, 3047-3050.
29. Gilbertson, S. R.; Xie, D. Angew. Chem., Int. Ed. 1999, 38, 2750-2752.
30. Knowles, W. S.; Sabacky, M. J. Chem. Commun. 1968, 22, 1445-1446.