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

被引：28

作者：

Hyatt, JA

Skelton, C

机构：

[1] Research Laboratories, Eastman Chemical Co., Kingsport

来源：

TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 04期

关键词：

D O I：

10.1016/S0957-4166(97)00020-7

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

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. (C) 1997 Elsevier Science Ltd.

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页码：523 / 526

页数：4

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