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Synthesis 1996; 1996(9): 1079-1081
DOI: 10.1055/s-1996-4348
short paper
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Synthesis of Enantiomerically Pure Mono-, Di- and Trisubstituted 2-Sulfinylbuta-1,3-dienes, via β-Hydroxy Selenides

Pascal Gosselin* , Eric Bonfand1 , Christian Maignan1
  • *Laboratoire de Synthèse Organique associé au C.N.R.S., Université du Maine, Avenue O. Messiean, BP 535, F-72017 Le Mans cedex, France, Fax +33(43)833366
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Publikationsdatum:
31. Dezember 2000 (online)

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α-Lithiated (+)-(R)-para-tolyl vinyl sulfoxide reacts with α-selanyl-carbonyl compounds to give the corresponding β-hydroxy selenides. Subsequent Krief-Reich elimination affords enantiomerically pure mono-, di- and trisubstituted 2-sulfinylbuta-1,3-dienes.

(+)-(R)-p-tolyl vinyl sulfoxide - 2-sulfinyldienes - β-hydroxy selenides - Krief-Reich elimination