Stereoselective Synthesis of Alcohols, III Stereochemistry of the Sigmatropic Rearrangement of (1-Cycloalkenylmethyl) Sulfoxides
Rearrangement of the chiral allyl sulfoxides 17 and 20 proceeded via the exo-transition state 14 to give the α-methylenecycloalkanols 18 and 21 in high enantiomeric purity.The extent of chirality transferred was less (44 and 60percent) on rearrangement of