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Synlett 2005(10): 1615-1617
DOI: 10.1055/s-2005-869867
DOI: 10.1055/s-2005-869867
LETTER
© Georg Thieme Verlag Stuttgart · New York
The Preparation of Enantiomerically Pure 3,4-Epoxy-1-butene and 3-Butene-1,2-diol
Further Information
Received
11 March 2005
Publication Date:
07 June 2005 (online)
Publication History
Publication Date:
07 June 2005 (online)
Abstract
Single enantiomer 2-hydroxy-3-butenyl tosylate is a key precursor for single enantiomer 3,4-epoxy-1-butene and 3-butene-1,2-diol. The epoxide results from ring-closure of the hydroxy-tosylate while the diol is obtained through the intermediacy of the corresponding cyclic carbonate. This latter sequence avoids the loss of enantiomeric purity observed through direct hydrolysis.
Key words
epoxides - asymmetric synthesis - chirality - diols - nucleophiles
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