First enantioselective synthesis of vinyl oxiranes from aldehydes and ylides generated from allyl halides and chiral sulfides |
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Authors: | Zanardi Jacques Lamazure David Minière Stéphanie Reboul Vincent Metzner Patrick |
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Institution: | Laboratoire de Chimie Moléculaire et Thio-organique (UMR CNRS 6507), ISMRA-Université de Caen, 6 Boulevard du Maréchal Juin, F-14050 Caen, France. |
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Abstract: | Asymmetric 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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