@article{pittir25624, volume = {71}, number = {3}, month = {January}, author = {P Wipf and T Tsuchimoto and H Takahashi}, title = {Synthetic applications of ortho esters}, journal = {Pure and Applied Chemistry}, pages = {415 -- 421}, year = {1999}, url = {http://d-scholarship-dev.library.pitt.edu/25624/}, 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 {\ensuremath{\alpha}}-amino, {\ensuremath{\alpha}}-hydroxy and {\ensuremath{\beta}}-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 {\ensuremath{\alpha}},{\ensuremath{\beta}}-unsaturated ortho esters and their use as homoenolate equivalents as well as the preparation of tertiary alcohols. {\copyright} 1999 IUPAC.} }