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Application of Sharpless asymmetric epoxidation on the preparation of the optically active flavours 3-methylthiohexanal and 5(6)-butyl-1,4-dioxan-2-one

✍ Scribed by Hong-yu Tian; Bao-guo Sun; Li-wei Tang; Hong-lin Ye

Publisher: John Wiley and Sons
Year: 2010
Tongue: English
Weight: 207 KB
Volume: 26
Category: Article
ISSN: 0882-5734
DOI: 10.1002/ffj.2017

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✦ Synopsis

Abstract

Optically active 2,3‐epoxyhexanol obtained from Sharpless asymmetric epoxidation (AE) was regioselectively reduced to 1,3‐hexandiol or 1,2‐hexandiol. 1,3‐Hexandiol was converted to 3‐mesyloxyhexyl acetate. The following reaction with CH~3~SK gave 3‐methylthiohexanol, which was oxidized through Swern oxidation to produce 3‐methylthiohexanal. 5‐ and 6‐Butyl‐1,4‐dioxan‐2‐one were formed concurrently by the reaction of 1,2‐hexandiol with 2‐bromoacetic chloride and the ratio of 5‐butyl isomer to 6‐butyl isomer was about 1:4. The enantiomeric excess values of both enantiomers of 3‐methylthiohexanal and 5(6)‐butyl‐1,4‐dioxan‐2‐one were about 90%, which were very close to those of 2,3‐epoxyhexanol (about 94% ee). No obvious racemization occurred during the transformation from the Sharpless AE products to the final products.

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