Enhanced diastereo and enantioselectivity in the formation of acyldithiolane sulphoxides by the asymmetric oxidation of their enolsilyl ethers

Tetrahedron Letters

Volumn 38, Issue 28, 1997, Pages 5047-5050

  Barros, M Teresa ^a,b   Leitão, Alcino J ^b   Maycock, Christopher D ^b,c  

^a UNIVERSIDADE NOVA DE LISBOA   (Portugal)

^b INSTITUTO DE TECNOLOGIA QUÍMICA E BIOLÓGICA   (Portugal)

^c UNIVERSITY OF LISBON   (Portugal)

Author keywords

[No Author keywords available]

Indexed keywords

ETHER DERIVATIVE; SILANE DERIVATIVE; SULFOXIDE;

ARTICLE; CRYSTALLIZATION; EPOXIDATION; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; STEREOCHEMISTRY; SULFATION;

HUMAN IMMUNODEFICIENCY VIRUS;

EID: 0030763953     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01101-5     Document Type: Article

References (8)

1. Page, P.C.B.; Namwindwa, E.S.; Klair, S.S.; Westwood, D. Synlett, 1990, 457.
2. Barros, M.T.; Leitäo, A.J.; Maycock, C.D. Tetrahedron Letters, 1995, 36, 6537. Traces of water can cause dramatic lowering of the diastereo-and enantioselectivities. See also reference 3.b).
3. a)Page, P.C.B.; Allihn, S.M.; Collingwood, E.W.; Carr, R.A.E. Tetrahedron Letters, 1994, 35, 2607. and references therein.
4. b) Aggarwal, V.K.; Evans, G.; Moya, E.; Dowden, J. J. Org. Chem., 1992, 57, 6390. The formation of the trans-dioxides of acyl dithiolanes is best carried out by periodate oxidation of the monosulphoxide and is completely diastereoselective.
5. Page, P.C.B.; Prodger, J.C. Synlett, 1990, 460.
6. Page, P.C.B.; Purdle, M.; Lathbury, D. Tetrahedron Letters, 1996, 37, 8929.
7. Di Furia, F.; Licini, G.; Modena, G. Gazz. Chim. Italiana, 1990, 120, 165.
8. For a related reaction see, Chen, C.H.; Donatelli, B.A. J. Org. Chem., 1976, 41, 3053.