TRANS-1,3-DITHIANE-1,3-DIOXIDE, A NEW CHIRAL ACYL ANION EQUIVALENT FOR THE PREPARATION OF MASKED ACTIVATED ACIDS - APPLICATION TO THE SYNTHESIS OF ALPHA-HYDROXY ACID-DERIVATIVES

Authors
AGGARWAL VK THOMAS A FRANKLIN RJ
Citation
Vk. Aggarwal et al., TRANS-1,3-DITHIANE-1,3-DIOXIDE, A NEW CHIRAL ACYL ANION EQUIVALENT FOR THE PREPARATION OF MASKED ACTIVATED ACIDS - APPLICATION TO THE SYNTHESIS OF ALPHA-HYDROXY ACID-DERIVATIVES, Journal of the Chemical Society, Chemical Communications, (14), 1994, pp. 1653-1654
Citations number
21
Categorie Soggetti
Chemistry
Journal title
Journal of the Chemical Society, Chemical Communications → ACNP
ISSN journal
00224936
Issue
14
Year of publication
1994
Pages
1653 - 1654
Database
ISI
SICI code
0022-4936(1994):14<1653:TANCAA>2.0.ZU;2-V
Abstract
trans-1,3-Dithiane-1,3-dioxide reacts with high diastereoselectivity w ith aromatic aldehydes and the 1,3-dithiane-1,3-dioxide moiety can be easily converted to a thiolester without racemisation by carrying out a Pummerer reaction; the thiolester is a group that can be readily tra nsformed into acids, esters, amides, ketones and aldehydes.