Z-selective horner-wadsworth-emmons-type reaction using a 10-P-5 phosphorane bearing bidentates derived from 1-naphthol

Chemistry Letters

Volumn 39, Issue 11, 2010, Pages 1138-1139

  Kojima, Satoshi ^a,b   Arimura, Jun Ya ^a   Kajiyama, Kazumasa ^c  

^a HIROSHIMA UNIVERSITY   (Japan)

^b HIROSHIMA UNIVERSITY   (Japan)

^c KITASATO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 78449309393     PISSN: 03667022     EISSN: 13480715     Source Type: Journal    
DOI: 10.1246/cl.2010.1138     Document Type: Article

References (38)

1. For leading reviews see: a) W. S. Wadsworth, Jr., in Organic Reactions, ed. by W. G. Dauben, John Wiley & Sons, New York, 1977, Vol. 25, pp. 73-253.
2. b) J. I. G. Cadogan, Organophosphorus Reagents in Organic Synthesis, Academic Press, New York, 1979.
3. c) B. E. Maryanoff, A. B. Reitz, Chem. Rev. 1989, 89, 863.
4. d) S. E. Kelly, in Comprehensive Organic Synthesis, ed. by B. M. Trost, I. Fleming, Pergamon Press, Oxford, 1991, Vol. 1, pp. 730-817.
5. e) A. W. Johnson, Ylides and !mines of Phosphorus, Wiley-Interscience, New York, 1993.
6. f) E. Vedejs, M. J. Peterson, Top. Stereochem. 1994, 21, 1.
7. g) E. Vedejs, M. J. Peterson, Adv. Carbanion Chem. 1996, 2, 1.
8. h) J. Clayden, S. Warren, Angew. Chem., Int. Ed. Engl. 1996, 35, 241.
9. i) O. I. Kolodiazhnyi, Phosphorus Ylides, Wiley-VCH, Weinheim, 1999.
10. j) K. Ando, J. Synth. Org. Chem., Jpn. 2000, 58, 869.
11. k) M. Edmonds, A. Abell, in Modern Carbonyl Olefination, ed. by T. Takeda, Wiley-VCH, Weinheim, 2004, pp. 1-17.
12. l) F. López-Ortiz, J. G. López, R. A. Manzaneda, I. J. P. Alvarez, Mini-Rev. Org. Chem. 2004, 1, 65.
13. W. C. Still, C. Gennari, Tetrahedron Lett. 1983, 24, 4405.
14. a) K. Ando, Tetrahedron Lett. 1995, 36, 4105.
15. b) K. Ando, J. Org. Chem. 1997, 62, 1934.
16. c) K. Ando, J. Org. Chem. 1998, 63, 8411.
17. d) K. Ando, J. Org. Chem. 1999, 64, 8406.
18. e) K. Kokin, J. Motoyoshiya, S. Hayashi, H. Aoyama, Synth. Commun. 1997, 27, 2387.
19. f) K. Ando, T. Oishi, M. Hirama, H. Ohno, T. Ibuka, J. Org. Chem. 2000, 65, 4745.
20. a) F. P. Touchard, N. Capelle, M. Mercier, Adv. Svnth, Catal, 2005, 347, 707.
21. b) F. P. Touchard, Eur. J. Org. Chem. 2005, 1790.
22. a) S. Kojima, H. Inai, T. Hidaka, K. Ohkata, Chem. Commun. 2000, 1795.
23. b) S. Kojima, H. Inai, T. Hidaka, T. Fukuzaki, K. Ohkata, J. Org. Chem. 2002, 67, 4093.
24. c) S. Kojima, T. Fukuzaki, A. Yamakawa, Y. Murai, Org. Lett. 2004, 6, 3917.
25. a) S. Kojima, R. Takagi, K.-y. Akiba, J. Am. Chem. Soc. 1997, 119, 5970.
26. b) S. Kojima, K. Kawaguchi, S. Matsukawa, K. Uchida, K.-y. Akiba, Chem. Lett. 2002, 170. For related mechanistic studies see:
27. c) S. Kojima, K.-y. Akiba, Tetrahedron Lett. 1997, 38, 547.
28. d) S. Kojima, K. Kawaguchi, K.-y. Akiba, Tetrahedron Lett. 1997, 38, 7753.
29. e) S. Matsukawa, S. Kojima, K. Kajiyama, Y. Yamamoto, K.-y. Akiba, S. Re, S. Nagase, J. Am. Chem. Soc. 2002,124, 13154.
30. f) S. Kojima, K. Kawaguchi, S. Matsukawa, K.-y. Akiba, Tetrahedron 2003, 59, 255.
31. M. L. Bojin, S. Barkallah, S. A. Evans, Jr., J. Am. Chem. Soc. 1996, 118, 1549.
32. a) K. Kajiyama, Y. Hirai, T. Otsuka, H. Yuge, T. K. Miyamoto, Chem. Lett. 2000, 784.
33. b) K. Kajiyama, H. Yuge, T. K. Miyamoto, Phosphorus, Sulfur Silicon Relat. Elem. 2002, 177, 1433.
34. c) K. !Kajiyama, A. Nakamoto, S. Miyazawa, T. K. Miyamoto, Chem. Lett. 2003, 32, 332.
35. d) K. Kajiyama, T. K. Miyamoto, K. Sawano, Inorg. Chem. 2006, 45, 502.
36. e) K. Kajiyama, I. Sato, S. Yamashita, T. K. Miyamoto, Eur. J. Inorg. Chem. 2009, 5516.
37. 4P 402.1021, found 402.1001.
38. 2Et (20.5 mg, 83%, Z:E = 96:4).