Oxirane ring-opening with alcohol catalyzed by organotin phosphate condensates. Complete inversion at tertiary and benzylic centers

J Otera, N Yoshihisa, N Hitosi

Index: Otera, Junzo; Niibo, Yoshihisa; Nozaki, Hitosi Tetrahedron, 1991 , vol. 47, # 36 p. 7625 - 7634

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Citation Number: 25

Abstract

Regio-and stereospecific ring-opening ofchiral 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 methodolgy is applied to synthesis of enantiomerically pure linalool and to conversion of commercially available (R)-styrene ...