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A kinetic resolution route to the (S)-chromanmethanol intermediate for synthesis of the natural tocols

✍ Scribed by John A. Hyatt; Chad Skelton

Publisher: Elsevier Science
Year: 1997
Tongue: English
Weight: 254 KB
Volume: 8
Category: Article
ISSN: 0957-4166
DOI: 10.1016/s0957-4166(97)00020-7

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✦ Synopsis

Kinetic resolution of 2-hydroxymethyl-2,5,7,8-tetramethyl-6-chromanol was carried out by reaction with succinic anhydride catalysed by Amano PS-30 lipase. The (S)-enantiomer (which corresponds to the natural (2R)-configuration of the natural tocopherols and tocotrienols) was selectively acylated. An enantiomeric excess of 96.5% was achieved, and the absolute configuration was proven by conversion to known tocol intermediates. This work provides an example of the uncommon kinetic resolution of a primary neopentyl-type alcohol and provides a high-yield, chromatography-free route to a useful tocol intermediate.

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