Stereoselective Synthesis of Alcohols, II Stereochemistry of the Sigmatropic Rearrangement of 3-Substituted 2-Alkenyl Sulfoxides
Rearrangement of the 3-E-substituted allyl sulfoxides 5 to the allyl alcohols 19 and 30 proceeds with low enantiomeric selectivity.In contrast, the 3-Z-substituted allyl sulfoxide 7b rearranged uniformly via the endo-transition state 26.