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First Enantioselective Synthesis of Vinyl Oxiranes from Aldehydes and Ylides Generated from Allyl Halides and Chiral Sulfides
journal contribution
posted on 2002-11-09, 00:00 authored by Jacques Zanardi, David Lamazure, Stéphanie Minière, Vincent Reboul, Patrick MetznerAsymmetric allylidenation of aldehydes with
sulfur ylides is possible with proper substitution of the initial
sulfide, to avoid the [2,3] sigmatropic rearrangement of the
unsaturated ylides. One-pot reaction of (2R,5R)-dimethylthiolane with allyl halides, aldehydes, and sodium hydroxide
in tert-butyl alcohol affords vinyl oxiranes in good yields.
Enantiomeric excesses up to 90% and trans selectivities have
been achieved with methallyl-type halides.
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Chiral Sulfides Asymmetric allylidenationbutyl alcoholAldehydeVinyl Oxiranesallyl halidessodium hydroxideFirst Enantioselective SynthesissigmatropicYlides GeneratedaldehydeAllyl Halidesdimethylthiolanesubstitutionvinyl oxiranessulfur ylidesterttrans selectivitiesyieldEnantiomeric excessesrearrangementsulfide
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