Chiral phosphine oxides and chiral esters in stereoselective intermolecular acylation reactions of phosphine oxides

Tetrahedron Letters

Volumn 37, Issue 41, 1996, Pages 7465-7468

  Cavalla, David ^a   Guéguen, Catherine ^a   Nelson, Adam ^a   O'Brien, Peter ^a   Russell, Matthew G ^a   Warren, Stuart ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHINE OXIDE DERIVATIVE;

ACYLATION; ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0030573987     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01612-7     Document Type: Article

References (19)

1. 1. Clayden, J.; Warren, S. Angew. Chem., Int. Ed. Engl., 1996, 35, 241-270.
2. 2. Buss, A. D.; Warren, S. J. Chem. Soc., Perkin Trans. 1, 1985, 2307-2325.
3. 3. Gemal, A. L.; Luche, J-L., J. Am. Chem. Soc., 1981, 103, 5454-5459.
4. 4. Hutton, G.; Jolliff, T.; Mitchell, H.; Warren, S. Tetrahedron Lett., 1995, 36, 7905-7908.
5. 5. Sometimes it is easier to synthesise β-keto phosphine oxides 2 by oxidation of the mixture of alcohols 3 obtained by reaction of alkyl phosphine oxides 1 with aldehydes. For examples, see refs 1 and 4.
6. 6. Buss, A. D.; Greeves, N.; Mason, R.; Warren, S. J. Chem. Soc., Perkin Trans. 1, 1987, 2569-2577; Torr, R. S.; Warren, S. J. Chem. Soc., Perkin Trans. 1, 1983, 1173-1179. See also refs 1 and 2.
7. 6. Buss, A. D.; Greeves, N.; Mason, R.; Warren, S. J. Chem. Soc., Perkin Trans. 1, 1987, 2569-2577; Torr, R. S.; Warren, S. J. Chem. Soc., Perkin Trans. 1, 1983, 1173-1179. See also refs 1 and 2.
8. 7. Ayrey, P. M.; Bolton, M. A.; Buss, A. D.; Greeves, N.; Levin, D.; Wallace, P.; Warren, S. J. Chem. Soc., Perkin Trans. 1, 1992, 3407-3417.
9. 8. We have reported an isolated example of the stereoselective intermolecular acylation of chiral phosphine oxide 7 with ethyl benzoate: Ayrey, P. M.; Warren, S. Tetrahedron Lett., 1989, 30, 4581-4584.
10. 9. Nelson, A.; Warren, S. Tetrahedron Lett., 1996, 37, 1501-1504; Feeder, N.; Hutton, G.; Warren, S. Tetrahedron Lett., 1994, 35, 5911-5914.
11. 9. Nelson, A.; Warren, S. Tetrahedron Lett., 1996, 37, 1501-1504; Feeder, N.; Hutton, G.; Warren, S. Tetrahedron Lett., 1994, 35, 5911-5914.
12. 10. Guéguen, C.; Mitchell, H. J.; O'Brien, P.; Warren, S. Tetrahedron Lett., 1996, 37, preceding paper.
13. 11. When we first reported this reaction (see ref 8), we incorrectly assigned the major product as anti-8.
14. 12. Fleming, I.; Lewis, J. J. J. Chem. Soc., Perkin Trans. 1, 1992, 3257-3266.
15. 13. Cavalla, D.; Cruse, W. B.; Warren, S. J. Chem. Soc., Perkin Trans. 1, 1987, 1883-1898.
16. 14. Kolb, H. C.; Sharpless, K. B. Tetrahedron, 1992, 48, 10515-10530.
17. 15. Wallace, P.; Warren, S. J. Chem. Soc., Perkin Trans. 1, 1988, 2971-2978.
18. 16. Our assignment of anti-14 is only tentative and will be verified later. For related addition reactions, see: Okuma, K.; Tanaka, Y.; Ohta, H.; Matsuyama, H. Bull. Chem. Soc. Jpn., 1993, 66, 2623-2632.
19. 17. O'Brien, P.; Warren, S. Tetrahedron Lett., 1996, 37, 4271-4274.