Excellent Z-Selective Olefin Formation Using Pentacoordinate Spirophosphoranes and Aldehydes. Wittig Type Reaction via Hexacoordinate Intermediates

Journal of the American Chemical Society

Volumn 119, Issue 25, 1997, Pages 5970-5971

  Kojima, Satoshi ^a   Takagi, Ryukichi ^a   Akiba, Kin Ya ^a  

^a HIROSHIMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000435980     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja964122w     Document Type: Article

References (26)

1. Cherkasoz, R. A.; Ploezhaeva. Ups. Khim. 1987, 56, 287-321.
2. Burgada, R.; Setton, R. In The Chemistry of Organophosphorus Compounds; Hartley, F. R., Ed.; Wiley-Interscience: Chichester, 1994.
3. Holmes, R. R. Chem. ReV. 1996, 96, 927-950.
4. Wong, C. Y.; Kennepohl, D. K.; Cavell, R. G. Chem. ReV. 1996, 96, 1917-1951.
5. Perkins, C. W.; Martin, J. C.; Arduengo, A. J.; Lau, W.; Alegria, A.; Kochi, J. K. J. Am. Chem. Soc. 1980, 102, 7753-7759.
6. Wadsworth, W. S., Jr. Org. React. 1977, 25, 73-253.
7. Cadogan, J. I. G. Organophosphorus Reagents in Organic Synthesis; Academic Press: New York, 1979.
8. Maryanoff, B. E.; Reitz, A. B. Chem. ReV. 1989, 89, 863-927.
9. Kelly, S. E. In ComprehensiVe Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 1, pp 730-817.
10. Johnson, A. W. Ylides and Imines of Phosphorus; Wiley-Interscience: New York, 1993.
11. Vedejs, E.; Peterson, M. J. Top. Stereochem. 1994, 21, 1-157.
12. (g) Clayden, J.; Warren, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 241-270.
13. Bojin, M. L.; Barkallah, S.; Evans, S. A., Jr. J. Am. Chem. Soc. 1996, 118, 1549-1550.
14. (a) Kojima, S.; Kajiyama, K.; Akiba, K.-Y. Bull. Chem. Soc. Jpn. 1995, 68, 1785-1797.
15. Kojima, S.; Kajiyama, K.; Akiba, K.-Y. Tetrahedron Lett. 1994, 35, 7037-7040.
16. Kojima, S.; Nakamoto, M.; Kajiyama, K.; Akiba, K.-Y. Tetrahedron Lett. 1995, 36, 2261-2264.
17. Kojima, S.; Akiba, K.-Y. Tetrahedron Lett. 1997, 38, 547-550.
18. Kawashima, T.; Watanabe, K.; Okazaki, R. Tetrahedron Lett. 1997, 38, 551-554.
19. Still, W. C; Gennari, C. Tetrahedron Lett. 1983, 24, 4405-4408.
20. Ando, K. Tetrahedron Lett. 1995, 36, 4105-4108.
21. (a) Granoth, I.; Martin, J. C. J. Am. Chem. Soc. 1979, 101, 4618-4622, 4623-4626.
22. Perozzi, E. F.; Michalak, R. S.; Figuly, G. D.; Stevenson, W. H., III; Dess, D. B.; Ross, M. R.; Martin, J. C. J. Org. Chem. 1981, 46, 1049-1053.
23. Thompson, S. K.; Heathcock, C. H. J. Org. Chem. 1990, 55, 3386-3388.
24. Vedejs, E.; Fleck, T. J. J. Am. Chem. Soc. 1989, 111, 5861-5871.
25. Kawashima, T.; Kato, K.; Okazaki, R. J. Am. Chem. Soc. 1992, 114, 4008-4010.
26. Kawashima, T.; Kato, K.; Okazaki, R. Angew. Chem., Int. Ed. Engl. 1993, 32, 869-870.