%A P Wipf
%A T Tsuchimoto
%A H Takahashi
%J Pure and Applied Chemistry
%T Synthetic applications of ortho esters
%X The zirconocene-catalyzed rearrangement of epoxy esters to give 2,7,8-trioxabicyclo[3.2.1]octanes (ABO-esters) adds a new modification to carboxylic acid chemistry. Acid/ base-sensitive ?-amino, ?-hydroxy and ?-bromo acid derivatives are converted in high yield to ABO-esters using this protocol. This strategy is complementary to the OBO-ester technology, and orthogonal methods for the deprotection of ABO-and OBO-esters have been developed. Using chiral epoxy alcohol derivatives, a convenient and general asymmetric synthesis of bicyclic ortho esters can be achieved. New applications of ABO-esters in organic synthesis include conjugate additions to ?,?-unsaturated ortho esters and their use as homoenolate equivalents as well as the preparation of tertiary alcohols. ? 1999 IUPAC.
%N 3
%P 415 - 421
%V 71
%D 1999
%R 10.1351/pac199971030415
%L pittir25624