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Synthesis 2009(3): 469-473
DOI: 10.1055/s-0028-1083322
DOI: 10.1055/s-0028-1083322
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Stereoselective Synthesis of Alkynyl Vinyl Chalcogenides via Horner-Wittig Reaction
Further Information
Received
4 September 2008
Publication Date:
09 January 2009 (online)
Publication History
Publication Date:
09 January 2009 (online)
Abstract
New (diphenylphosphoryl)methyl phenylethynyl sulfides, selenides, or tellurides were prepared by the reaction of (diphenylphosphoryl)methyl p-toluenesulfonate with alkynethiols, -selenols, or -tellurols at room temperature. The (diphenylphosphoryl)methyl phenylethynyl sulfides, selenides, or tellurides reacted with aldehydes and cyclic ketones to give the corresponding alkynyl vinyl sulfides, selenides, or tellurides, with preferential E-stereochemistry, in a Horner-Wittig-type reaction.
Key words
Wittig reaction - alkynyl vinyl chalcogenides - vinyl chalcogenides - chalcogenium - olefination
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