Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 67, Issue 25, Pages 9083-9086Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo026085z
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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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