Asymmetric dihydroxylation and hydrogenation approaches to the enantioselective synthesis of R-(+)-alpha-lipoic acid

Authors
Upadhya, TT Nikalje, MD Sudalai, A
Citation
Tt. Upadhya et al., Asymmetric dihydroxylation and hydrogenation approaches to the enantioselective synthesis of R-(+)-alpha-lipoic acid, TETRAHEDR L, 42(29), 2001, pp. 4891-4893
Citations number
24
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
29
Year of publication
2001
Pages
4891 - 4893
Database
ISI
SICI code
0040-4039(20010716)42:29<4891:ADAHAT>2.0.ZU;2-J
Abstract
The asymmetric synthesis of methyl (S)-6,8-dihydroxyoctanoate (5) and (S)-6 ,8-dimethylsulfonyloxyoctane-1 -car boxylic acid (13), key precursors to R- (+)-alpha -lipoic acid (6) is described using OsO4-catalyzed asymmetric dih ydroxylation and Ru-catalyzed asymmetric hydrogenation, respectively, as th e key steps in the reaction sequence. These methods lead to an efficient fo rmal synthesis of R-(+)-alpha -lipoic acid in 90%, ee. (C) 2001 Elsevier Sc ience Ltd. All rights reserved.