Oxirane Ring-Opening with Alcohol Catalyzed by Organotin Phosphate Condensates. Complete Inversion at Tertiary and Benzylic Centers

Article abstract of DOI:10.1016/S0040-4020(01)88286-7

Regio- and stereospecific ring-opening of chiral oxiranes has been effected by organotin phosphate condensates catalyst.Alcohols attack on the tertiary and benzylic positions exclusively.Despite seemingly acidic character of the catalyst in terms of regioselectivity the chiral centers are completely inverted.The new methodology is applied to synthesis of enantiomerically pure linalool and to conversion of commercially available (R)-styrene oxide into the (S)-counterpart.