Kinetic resolution of P-Chirogenic compounds by palladium-catalyzed alcoholysis of vinyl ethers

Advanced Synthesis and Catalysis

Volumn 351, Issue 11-12, 2009, Pages 1796-1800

  Itoh, Hisashi ^a   Yamamoto, Eiji ^a   Masaoka, Shigeyuki ^a   Sakai, Ken ^a   Tokunaga, Makoto ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

Alcoholysis; Chirality; Kinetic resolution; Phosphorus

Indexed keywords

EID: 68949163234     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200900304     Document Type: Article

References (47)

1. a) W. S. Knowles, Angew. Chem. 2002, 114, 2096-2107;
2. Angew. Chem. Int. Ed. 2002, 41, 1998-2007;
3. b) K. V. L. Crépy, T. Imamoto, Adv. Synth. Catal. 2003, 345, 79-101;
4. c) T. Nemoto, T. Matsumoto, T. Masuda, T. Hitomi, K. Hatano, Y. Hamada, J. Am. Chem. Soc. 2004, 126, 3690-3691.
5. a) L. A. Spangler, M. Mikolajczyk, E. L. Burdge, P. Kielbasinski, H. C. Smith, P. Lyzwa, J. D. Fisher, J. Omelanczuk, J. Agric. Food Chem. 1999, 47, 318-321;
6. b) S. Zhou, K. Lin, H. Yang, L. Li, W. Liu, J. Li, Chem. Res. Toxicol. 2007, 20, 400-405;
7. c) C. M. Hill, W.-S. Li, T.-C. Cheng, J.J. DeFrank, F.M. Raushel, Bioorg. Chem. 2001, 29, 27-35;
8. d) T. Sato, H. Ueda, K. Nakagawa, N. Bordor, J. Org. Chem. 1983, 48, 98-101;
9. e) L. A. Wozniak, M. Janicka, M. Bukowiecka-Matusiak, J. Organomet. Chem. 2005, 690, 2658-2663.
10. J. Meisenheimer, L. Lichtenstadt, Ber. dtsch. chem. Ges. 1911, 44, 356-359.
11. a) Y. Li, S. D. Aubert, E. G. Maes, F. M. Raushel, J. Am. Chem. Soc. 2004, 126, 8888-8889;
12. b) K. Shioji, Y. Ueno, Y. Kurauchi, K. Okuma, Tetrahedron Lett. 2001, 42, 6569-6571.
13. a) A. R. Muci, K. R. Campos, D. A. Evans, J. Am. Chem. Soc. 1995, 117, 9075-9076;
14. b) T. Imamoto, J. Watanabe, Y. Wada, H. Masuda, H. Yamada, H. Tsuruta, S. Matsukawa, K. Yamaguchi, J. Am. Chem. Soc. 1998, 120, 1635-1636;
15. c) C. Strohmann, K. Strohfeld, D. Schildbach, M. J. McGrath, P. O'Brien, Organometallics 2004, 23, 5389-5391;
16. d) S. Juge, M. Stephan, J. A. Laffitte, J. P. Genet, Tetrahedron Lett. 1990, 31, 6357-6360;
17. e) C. Genet, S. J. Canipa, P. O'Brien, S. Taylor, J. Am. Chem. Soc. 2006, 128, 9336-9337;
18. f) H. Lebel, S. Morin, V Paquet, Org. Lett. 2003, 5, 2347-2349;
19. g) G. Nishida, K. Noguchi, M. Hirano, K. Tanaka, Angew. Chem. 2008, 120, 3458-3461;
20. Angew. Chem. Int. Ed. 2008, 47, 3410-3413;
21. h) N. F. Blank, J. R. Moncarz, T. J. Brunker, C. Scriban, B. J. Anderson, O. Amir, D. S. Glueck, L. N. Zakharov, J. A. Golen, C. D. Incarvito, A. L. Rheingold, J. Am. Chem. Soc. 2007, 129, 6847-6858;
22. i) V. S. Chan, I. C. Stewart, R. G. Bergman, F. D. Toste, J. Am. Chem. Soc. 2006, 128, 2786-2787;
23. j) E. Bergin, C. T. O'Connor, S. B. Robinson, E. M. McGarrigle, C. P. O'Mahony, D. G. Gilheany, J. Am. Chem. Soc. 2007, 129, 9566-9567;
24. k) V. S. Chan, M. Chiu, R. G. Bergman, F. D. Toste, J. Am. Chem. Soc. 2009, 131, 6021-6032.
25. R. Noyori, M. Tokunaga, M. Kitamura, Bull. Chem. Soc. Jpn. 1995, 68, 36-55.
26. a) J. Liang, J. C. Ruble, G. C. Fu, J. Org. Chem. 1998, 63, 3154-3155;
27. b) Y. Chen, P. McDaid, L. Deng, Chem. Rev. 2003, 103, 2965-2983;
28. c) H. Aoyama, M. Tokunaga, S. Hiraiwa, Y. Shirogane, Y. Obora, Y. Tsuji, Org. Lett. 2004, 6, 509-512;
29. d) H. Aoyama, M. Tokunaga, J. Kiyosu, T. Iwasawa, Y. Obora, Y. Tsuji, J. Am. Chem. Soc. 2005, 127, 10474-10475;
30. e) M. Tokunaga, J. Kiyosu, Y. Obora, Y. Tsuji, J. Am. Chem. Soc. 2006, 128, 4481-4486;
31. f) S. Tanaka, H. Saburi, M. Kitamura, Adv. Synth. Catal. 2006, 348, 375-378;
32. g) T. Sakuma, E. Yamamoto, H. Aoyama, Y. Obora, Y. Tsuji, M. Tokunaga, Tetrahedron: Asymmetry 2008, 19, 1593-1599;
33. h) A. Nakamura, M. Tokunaga, Tetrahedron Lett. 2008, 49, 3729-3732;
34. i) C. I. Maxwell, K. Shah, P. V. Samuleev, A. A. Nevrov, R. S. Brown, Org. Biomol. Chem. 2008, 6, 2796-2803;
35. j) T. Hirakawa, S. Tanaka, N. Usuki, H. Kanzaki, M. Kishimoto, M. Kitamura, Eur. J. Org. Chem. 2009, 789-792.
36. a) B. Dhawan, D. Redmore, J. Org. Chem. 1986, 57, 179-183;
37. b) K. A. Petrov, S.V. Agafonov, V.P. Pokatun, Zhur. Obshch. Khim. 1987, 57, 98-101;
38. c) J. Heinicke, E. Nietzschmann, K. Kellner, A. Tzschach, R. Kadyrov, German Patent (East), DDR 276872, 1990;
39. d) L. D. Popov, G. I. Bondarenko, A. A. Shvets, L. N. Etmetchenko, Zhur. Obshch. Khim. 1991, 61, 300-304;
40. e) A, Vernek, L. Troxler, G. Wipff, Chem. Eur. J. 1997, 3, 552-560;
41. f) J. Heinicke, U. Jux, R. Kadyrov, M. He, Heteroat. Chem. 1997, 8, 383-395;
42. g) V. P. Solov'ev, V. E. Baulin, N. N. Strakhova, V. P. Kazachenko, V. K. Belsky, A. A. Varnek, T. A. Volkova, G. Wipff, J. Chem. Soc. Perkin Trans. 2 1998, 1489-1498;
43. h) L, Xie, J. Ma, Y.-X. Ding, Tetrahedron Lett. 2008, 49, 847-850;
44. i) P, Huszthy, V. Farkas, T. Tóth, G, Székely, M. Hollósi, Tetrahedron 2008, 64, 10107-10115.
45. M. Blouin, R. Frenette, J. Org. Chem. 2001, 66, 9043-9045.
46. T. Iwasawa, M. Tokunaga, Y. Obora, Y. Tsuji, J. Am. Chem. Soc. 2004, 126, 6554-6555;
47. Y. Tsuji, T. Fujihara, Inorg. Chem. 2007, 46, 1895-1902.