Cesium Fluoride-Mediated Horner-Wittig Addition Reactions of Silyl Phosphine Oxides; Synthesis of Optically Active Silyl Phosphine Oxides Using Chiral Bases and a Chiral Acid

Synlett

Volumn 1996, Issue 6, 1996, Pages 579-581

  O'Brien, Peter ^a   Warren, Stuart ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001495728     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5488     Document Type: Article

References (18)

1. Buss, A. D.; Warren, S. J. Chem. Soc., Perkin Trans. 1, 1985, 2307.
2. (a) McDougal, P. G.; Condon, B. D. Tetrahedron Lett., 1989, 30, 789;
3. (b) Lamothe, M.; Anderson, M. B.; Fuchs, P. L. Synth. Commun., 1991, 21, 1675;
4. (c) Kawashima, T.; Mitsuda, N.; Inamoto, N. Bull. Chem. Soc. Jpn., 1991, 64, 708.
5. (a) Vedejs, E.; Martinez, G. R. J. Am. Chem. Soc., 1979, 101, 6452;
6. (b) Bestmann, H. J.; Bombard, A. Angew. Chem., Int. Ed. Engl., 1982, 21, 545;
7. (c) Kawashima, T.; Ishii, T.; Inamoto, N. Bull. Chem. Soc. Jpn., 1987, 60, 1831.
8. +), 216 (80, M - PhCHO) and 215 (100, M - PhCHOH).
9. For leading references on chiral bases 5-9, see: (a) Cox, P. J.; Simpkins, N. S. Tetrahedron: Asymmetry, 1991, 2, 1; (b) Knochel, P. Angew. Chem., Int. Ed. Engl., 1992, 31, 1459; (c) Hodgson, D.; Witherington, J.; Moloney, B. A. Tetrahedron: Asymmetry, 1994, 5, 337.
10. For leading references on chiral bases 5-9, see: (a) Cox, P. J.; Simpkins, N. S. Tetrahedron: Asymmetry, 1991, 2, 1; (b) Knochel, P. Angew. Chem., Int. Ed. Engl., 1992, 31, 1459; (c) Hodgson, D.; Witherington, J.; Moloney, B. A. Tetrahedron: Asymmetry, 1994, 5, 337.
11. For leading references on chiral bases 5-9, see: (a) Cox, P. J.; Simpkins, N. S. Tetrahedron: Asymmetry, 1991, 2, 1; (b) Knochel, P. Angew. Chem., Int. Ed. Engl., 1992, 31, 1459; (c) Hodgson, D.; Witherington, J.; Moloney, B. A. Tetrahedron: Asymmetry, 1994, 5, 337.
12. (a) Simpkins, N. S. Chem. Ind. (London), 1988, 387;
13. (b) Persad, A; Simpkins, N. S. reported in reference 5a.
14. Cain, C. M.; Cousins, R. P. C.; Coumbarides, G.; Simpkins, N. S. Tetrahedron, 1990, 46, 523.
15. Pirkle, W. H.; Sikkenga, D. L.; Pavlin, M. S. J. Org. Chem., 1977, 42, 384.
16. Vedejs, E.; Garcia-Rivas, J. A. J. Org. Chem., 1994, 59, 6517.
17. Using the deracemisation conditions described in Table 3, we obtained (5)-1-diphenylphosphinoyl-1-phenylethane in 77% yield with 74% ee, a result which is consistent with that reported by Vedejs. 9 Interestingly, replacement of the phenyl ring with a cyclohexenyl group led to a dramatic decrease in the selectivity: 1-(1-diphenylphosphinoylethyl)cyclohexene was obtained in 63% yield but with only 20% ee.
18. We have already demonstrated that lithiated phosphine oxides are not configurationally stable: O'Brien, P.; Warren, S. Tetrahedron Lett., 1995, 36, 8473.