Total synthesis of (R)-lipoic acid and (S)-lipoic acid via an Mn (III)-salen-catalyzed oxidative kinetic resolution

TitleTotal synthesis of (R)-lipoic acid and (S)-lipoic acid via an Mn (III)-salen-catalyzed oxidative kinetic resolution
Publication TypeJournal Article
Year of Publication2015
AuthorsPurude, AN, Pawar, KP, Patil, NB, Kalkote, UR, Chavan, SP
JournalTetrahedron-Asymmetry
Volume26
Issue5-6
Pagination281-287
Date PublishedMAR
ISSN0957-4166
Abstract

The asymmetric synthesis of both the antipodes of alpha-lipoic acid is described. The total synthesis of racemic and asymmetric lipoic acid is achieved from propane 1,3-diol. This work reports the use of Mn (III)-salen-catalyzed oxidative kinetic resolution as the key step to obtain enantiomerically pure (R)- and (S)-lipoic acid. The undesired product formed during the resolution can be recycled to achieve the desired isomer. (C) 2015 Elsevier Ltd. All rights reserved.

DOI10.1016/j.tetasy.2015.02.001
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)2.108
Divison category: 
Organic Chemistry