Asymmetric dithioacetals II: A novel and versatile method for the preparation of chiral dithioacetals

Journal Article (Journal Article)

Reaction of aldehydes with one equivalent each of a thiol and a chiral thiolacid such as (R)-(-)-α-methoxyphenylthiolacetic acid in the presence of an acidic catalyst such as ZnI2 or p-toluenesulfonic acid yields diastereomeric mixed thioacetals in good yields which are generally readily separable. Subsequent deacylation at low temperature with sodium methoxide and alkylation of the resulting thiolate anion with a variety of electrophiles provides chiral dithioacetals with no loss of enantiomeric purity. © 1988.

Full Text

Duke Authors

Cited Authors

  • Thérien, M; Gauthier, JY; Young, RN

Published Date

  • January 1, 1988

Published In

Volume / Issue

  • 29 / 51

Start / End Page

  • 6733 - 6736

International Standard Serial Number (ISSN)

  • 0040-4039

Digital Object Identifier (DOI)

  • 10.1016/S0040-4039(00)82441-7

Citation Source

  • Scopus