Palladium-Catalyzed Insertion of α-Diazoesters into Vinyl Halides To Generate α,β-Unsaturated γ-Amino Esters

Angewandte Chemie - International Edition

Volumn 48, Issue 20, 2009, Pages 3677-3680

  Kudirka, Romas ^a   Devine, Sean K J ^a   Adams, Christopher S ^a   Van Vranken, David L ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Amino acids; C C coupling; Diazo compounds; Palladium; Peptide mimics

Indexed keywords

AMINO ESTERS; C - C COUPLING; CARBENES; DIAZO COMPOUNDS; PEPTIDE MIMICS; SIDE CHAINS; SINGLE-STEP; SYNTHETIC APPROACH; THREE-COMPONENT COUPLING; VINYL HALIDES; VINYL SUBSTITUENTS;

AMINATION; AMINO ACIDS; ESTERS; ORGANIC ACIDS; PALLADIUM; PALLADIUM COMPOUNDS; PEPTIDES;

AMINES;

EID: 70349971076     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200805483     Document Type: Article

References (35)

1. a) R. Kudirka, D. L. Van Vranken,J. Org. Chem. 2008, 73, 3585-3588;
2. b) S. K. J. Devine, D. L. Van Vranken, Org. Lett. 2008, 10, 1909-1911;
3. c)S. K. J. Devine, D. L. Van Vranken, Org. Lett. 2007, 9, 2047-2049;
4. d) K. L. Greenman, D. L. Van Vranken, Tetrahedron 2005, 61, 6438-6441;
5. e) K. L. Greenman, D. S. Carter, D. L. Van Vranken, Tetrahedron 2001, 57, 5219-5225.
6. a) J. E. Coleman, E. D. de Silva, K. Fangming, R. J. Andersen, T. M. Allen, Tetrahedron 1995, 51, 10653-10662;
7. b) N. Schaschke, Bioorg. Med. Chem. Lett. 2004, 14, 855-858.
8. For a review of Michael acceptors (including a,b-unsaturated-g- aminoesters) as protease inhibitors, see: M. M. M. Santos, R. Moreira, Mini-Rev. Med. Chem. 2007, 7, 1040-1050, and references therein.
9. a) S. Hanessian, X. Luo, R. Schaum, S. Michnick, J. Am. Chem. Soc. 1998, 120, 8569-8570;
10. b) T. Hintermann, K. Gademann, B. Jaun, D. Seebach, Helv. Chim. Acta 1998, 81, 983-1002;
11. c) S. Hanessian, X. H. Luo, R. Schaum, Tetrahedron Lett. 1999, 40, 4925-4929;
12. d) D. Seebach, M. Brenner, M. Rueping, B. Schweizer, B. Juan, Chem. Commun. 2001, 207-208;
13. e) C. Baldauf, R. Gunther, H. J. Hofmann, Helv. Chim. Acta 2003, 86, 2573-2588;
14. f) for an example of a sheetlike structure, see: M. G. Woll, J. R. Lai, I. A. Guzei, S. J. C. Taylor, M. E. B. Smith, S. H. Gellman,J. Am. Chem. Soc. 2001, 123, 11077-11078.
15. a) I Jurczak, A. Golebiowski, Chem. Rev. 1989, 89, 149-164;
16. b) z.ast;D. Yoo, J. S. Oh, Y. G. Kim, Org. Lett. 2002, 4, 1213-1215;
17. c) z.ast;L. K. Blasdel, A. G. Myers, Org. Lett. 2005, 7, 4281-4283.
18. C. Peng, Y. Wang, J. Wang, J. Am. Chem. Soc. 2008, 130, 1566-1567.
19. a) S. Ogoshi, T. Morimoto, K. Nishio, K. Ohe, S. Murai, J. Org. Chem. 1993, 58, 9-10;
20. b) N. Monteiro, J. Gore, B. Van Hemel- ryck, G. Balme, Synlett 1994, 447-449;
21. c) N. Monteiro, G. Balme, J. Org. Chem. 2000, 65, 3223-3226;
22. d) E. Fillion, N.J. Taylor, J. Am. Chem. Soc. 2003, 125, 12700-12701;
23. e) V. E. Trepanier, E. Fillion, Organometallics 2007, 26, 30-32;
24. f) J. M. Goll, E. Fillion, Organometallics 2008, 27, 3622-3625.
25. C. Peng, J. Cheng, J. Wang, J. Am. Chem. Soc. 2007, 129, 8708-8709.
26. a) E. Ihara, N. Haida, M. Iio, K. Inoue, Macromolecules 2003, 36, 36-41;
27. b) E. Ihara, M. Kida, M. Fujioka, N. Haida, T. Itoh, K. Inoue, J. Polym. Sci. Part A 2007, 45, 1536-1545.
28. M. P. Di, K. S. Rein, Tetrahedron Lett. 2004, 45, 4703-4706.
29. M. Broring, C. D. Brandt, S. Stellwag, Chem. Commun. 2003, 2344-2345.
30. a) A. C. Albeniz, P. Espinet, R. Manrique, A. Perez-Mateo, Angew. Chem. 2002, 114, 2469-2472;
31. Angew. Chem. Int. Ed. 2002, 41, 2363-2366;
32. b) A. A. Danopoulos, N. Tsoureas, J. C. Green, M. B. Hursthouse, Chem. Commun. 2003, 756-757.
33. R. Tanikaga, J. Takeuchi, M. Takyu, A. Kaji, J. Chem. Soc. Chem. Commun. 1987, 386-387.
34. R. Kumareswaran, Y. D. Vankar, Synth. Commun. 1998, 28, 2291-2302.
35. L. Benati, D. Nanni, P. Spagnolo, J. Org. Chem. 1999, 64, 5132-5138.