SYNTHESIS OF SILICON SUBSTITUTED CYCLOPROPYLMETHYL ALCOHOLS IN OPTICALLY-ACTIVE FORM VIA ASYMMETRIC SIMMONS-SMITH REACTION OF GAMMA-SILICON SUBSTITUTED ALLYLIC ALCOHOLS

Optically active silicon substituted cyclopropylmethyl alcohols were synthesized through asymmetric Simmons-Smith reaction; that is, the reaction of gamma-silicon substituted allylic alcohols with diethylzinc and diiodomethane utilizing (+)-diethyl tartrate as a chiral auxiliary was found to afford the corresponding silicon substituted cyclopropylmethyl alcohols with high stereoselectivity up to 92% ee.