REGIOSPECIFIC AND STEREOSPECIFIC SYNTHESIS OF (O-TIPS)-PROTECTED 2-HYDROXYALKYLMERCAPTANS FROM EPOXIDES AND TRIISOPROPYLSILANETHIOL

Authors
DEPOMAR JCJ SODERQUIST JA
Citation
Jcj. Depomar et Ja. Soderquist, REGIOSPECIFIC AND STEREOSPECIFIC SYNTHESIS OF (O-TIPS)-PROTECTED 2-HYDROXYALKYLMERCAPTANS FROM EPOXIDES AND TRIISOPROPYLSILANETHIOL, Tetrahedron letters, 39(25), 1998, pp. 4409-4412
Citations number
8
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
25
Year of publication
1998
Pages
4409 - 4412
Database
ISI
SICI code
0040-4039(1998)39:25<4409:RASSO(>2.0.ZU;2-E
Abstract
The regiospecific ring-opening of both mono-and disubstituted epoxides with triisopropylsilanethiol/DBU has been developed to provide 2-trii sopropylsilyloxyalkylthiols (I) in high yields. Non-racemic 1 is easil y prepared from optically active epoxides. Moreover, the further elabo ration of 1, through the exposed mercapto functionality, provides cont rolled access to unsymmetrical mono-protected bis-(2-hydroxyalkyl) sul fides and functionalized thioesters. (C) 1998 Elsevier Science Ltd. Al l rights reserved.