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Synthesis 2008(20): 3299-3306  
DOI: 10.1055/s-0028-1083162
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Novel Approach to γ-Hydroxy-α,β-unsaturated Compounds

Henryk Krawczyk*, Katarzyna Wąsek, Jacek Kędzia
Institute of Organic Chemistry, Technical University of Łódź, Żeromskiego 116, 90-924 Łódź, Poland
Fax: +48(42)6365530; e-Mail: henkrawc@p.lodz.pl;
Further Information

Publication History

Received 17 June 2008
Publication Date:
25 September 2008 (online)

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Abstract

A simple synthesis of (E)-alk-1-enyl mesylates from (E)-alk-1-enylphosphonates is reported. Construction of γ-hydroxy-α,β-unsaturated compounds was achieved by a two-step process involving dihydroxylation of the enol mesylates followed by HWE reaction of the resulting α-hydroxy aldehydes with activated methylphosphonates. Enantioselective synthesis of the title compounds is also reported.

Key words

alk-1-enyl mesylates - dihydroxylation - α-hydroxy aldehydes - Horner-Wadsworth-Emmons reaction - Conant-Swan fragmentation

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