Asymmetric dihydroxylation and hydrogenation approaches to the enantioselective synthesis of R-(+)-α-lipoic acid
TT Upadhya, MD Nikalje, A Sudalai - Tetrahedron Letters, 2001 - Elsevier
The asymmetric synthesis of methyl (S)-6, 8-dihydroxyoctanoate (5) and (S)-6, 8-
dimethylsulfonyloxyoctane-1-carboxylic acid (13), key precursors to R-(+)-α-lipoic acid (6) is
described using OsO4-catalyzed asymmetric dihydroxylation and Ru-catalyzed asymmetric
hydrogenation, respectively, as the key steps in the reaction sequence. These methods lead
to an efficient formal synthesis of R-(+)-α-lipoic acid in 90% ee.
dimethylsulfonyloxyoctane-1-carboxylic acid (13), key precursors to R-(+)-α-lipoic acid (6) is
described using OsO4-catalyzed asymmetric dihydroxylation and Ru-catalyzed asymmetric
hydrogenation, respectively, as the key steps in the reaction sequence. These methods lead
to an efficient formal synthesis of R-(+)-α-lipoic acid in 90% ee.
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