Journal
TETRAHEDRON-ASYMMETRY
Volume 20, Issue 24, Pages 2802-2808Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetasy.2009.11.005
Keywords
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Funding
- Ministry of Education, Culture, Sports and Science and Technology, Japan [21550051]
- Grants-in-Aid for Scientific Research [21550051] Funding Source: KAKEN
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The deracemization of 1,2-diol monotosylate derivatives is achieved by the sequential combination of enzymatic hydrolysis and Mitsunobu inversion using a polymer-bound triphenylphosphine. After the lipase-catalysed hydrolysis of the racemic 2-acetoxyhexyl tosylate, the subsequent Mitsunobu reaction without separation causes an inversion of the resulting (R)-alcohol to give the (S)-enantiomer of the acetate as a single product. In particular, the reaction using the polymer-bound triphenylphosphine also proceeds smoothly, and the product is easily separated by filtration from the polymer-bound reagent and its by-products. This deracemization process is applicable to the preparation of several optically active 1,2-diol monotosylates. (C) 2009 Elsevier Ltd. All rights reserved.
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