Diastereoselective reactions of optically active γ-substituted vinyl phosphine oxides

Tetrahedron Letters

Volumn 38, Issue 19, 1997, Pages 3471-3474

  Clayden, Jonathan ^a,b   Nelson, Adam ^a,b   Warren, Stuart ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^b UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHINE OXIDE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030919222     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00658-8     Document Type: Article

References (31)

1. Minami, T.; Motoyoshiya J. Synthesis, 1992, 333-349; Baldwin, I. C.; Beckett, R. P.; Williams, J. M. J. Synthesis, 1996, 34-36.
2. Minami, T.; Motoyoshiya J. Synthesis, 1992, 333-349; Baldwin, I. C.; Beckett, R. P.; Williams, J. M. J. Synthesis, 1996, 34-36.
3. Collins, D. J.; Mollard, S.-A.; Rose, N.; Swan, J. M. Aust. J. Chem., 1974, 27, 2365-2372.
4. Cavalla, D.; Cruse, W. B.; Warren, S. J. Chem. Soc., Perkin Trans. 1, 1987, 1883-1898.
5. Pietrusiewicz, K. M.; Zablocka, M.; Monkiewicz, J. J. Org. Chem., 1984, 49, 1522-1526.
6. Fleming, I.; Gil, S.; Sarkar, A. K.; Schmidlin, T. J. Chem. Soc., Perkin Trans. 1, 1992, 3351-3361.
7. Brandi, A.; Cannarò P.; Pietrusiewicz K. M.; Zablocka, M.; Wieczorek, M. J. Org. Chem., 1989, 54, 3073-3077;
8. Brandi, A.; Cicchi, S.; Goti, A.; Pietrusiewicz, K. M. Gazz. Chim. Ital., 1991, 121, 285-295.
9. Hall, D.; Sévin, A.-F.; Warren, S. Tetrahedron Lett., 1991, 32, 7123-7126.
10. Clayden, J.; Collington, E. W.; Lamont, R. B.; Warren, S. Tetrahedron Lett., 1993, 34, 2203-2206.
11. Guéguen, C.; O'Brien, P.; Warren, S.; Wyatt, P. J. Organomet. Chem., 1997, in the press.
12. Nelson, A.; Warren, S. Tetrahedron Lett., 1996, 37, 1501-1504.
13. Bennani, Y. L.; Sharpless, K. B. Tetrahedron Lett., 1993, 34, 2083-2086.
14. Nelson, A.; O'Brien, P.; Warren, S. Tetrahedron Lett., 1995, 36, 2685-2688; Nelson, A.; Warren, S J. Chem. Soc., Perkin Trans. 1, 1997, in the press, paper number 7/00374I.
15. Nelson, A.; O'Brien, P.; Warren, S. Tetrahedron Lett., 1995, 36, 2685-2688; Nelson, A.; Warren, S J. Chem. Soc., Perkin Trans. 1, 1997, in the press, paper number 7/00374I.
16. 12
17. Attempted protections of vinyl phosphine oxides (e.g. 10d) using strongly basic reaction conditions precipitated tautomerisation to the corresponding γ-keto phosphine oxides (e.g. 14). Equation Presented
18. Okuma K.; Tanaka, Y.; Ohta, H.; Matsuyama, H. Bull. Chem. Soc. Jpn., 1993, 66, 2623-2632.
19. 10
20. Feeder, N.; Hutton, G.; Warren, S. Tetrahedron Lett., 1994, 35, 5911-5914.
21. We were unable to synthesise alcohols 13 by asymmetric hydroboration of the corresponding allylic phosphine oxides: G. Hutton and S. Warren, unpublished results.
22. Domínguez, E.; Carretero, J. C. Tetrahedron Lett., 1993, 34, 5803-5806.
23. A mechanism for this tautomerisation is proposed in footnote 14.
24. Ager, D.J.; Fleming, I.; Patel, S. K. J. Chem. Soc., Perkin Trans. 1, 1981, 2520-2532.
25. Silyl ether 17b was even less stable, and decomposed to 19 on standing in deuterochloroform.
26. Ager, D.J.; "The Peterson Olefination Reaction", in Organic Reactions, ed. Paquette, L. A., vol. 38, 1990, p. 1.
27. 25
28. Yamamoto, Y.; Chounan, Y.; Nishii, S.; Ibuka, T.; Kitahara, H. J. Am. Chem. Soc., 1992, 114, 7652-7660.
29. Clayden, J.; Warren, S. J. Chem. Soc., Perkin Trans. 1, 1994, 2811-2823.
30. Jackson, R. F. W.; Standen, S. P.; Clegg, W. Tetrahedron Lett., 1991, 32, 5393-5396; Hirama, M.; Hioki, H.; Itô, S.; Kabuto, C. Tetrahedron Lett., 1988, 29, 3121-3124.
31. Jackson, R. F. W.; Standen, S. P.; Clegg, W. Tetrahedron Lett., 1991, 32, 5393-5396; Hirama, M.; Hioki, H.; Itô, S.; Kabuto, C. Tetrahedron Lett., 1988, 29, 3121-3124.