Wipf, P and Tsuchimoto, T and Takahashi, H
(1999)
Synthetic applications of ortho esters.
Pure and Applied Chemistry, 71 (3).
415 - 421.
ISSN 0033-4545
Abstract
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.
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