%0 Journal Article
%@ 0033-4545
%A Wipf, P
%A Tsuchimoto, T
%A Takahashi, H
%D 1999
%F pittir:25624
%J Pure and Applied Chemistry
%N 3
%P 415 - 421
%T Synthetic applications of ortho esters
%U http://d-scholarship-dev.library.pitt.edu/25624/
%V 71
%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 α-amino, α-hydroxy and β-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 α,β-unsaturated ortho esters and their use as homoenolate equivalents as well as the preparation of tertiary alcohols. © 1999 IUPAC.