TY  - JOUR
ID  - pittir25624
UR  - http://d-scholarship-dev.library.pitt.edu/25624/
IS  - 3
A1  - Wipf, P
A1  - Tsuchimoto, T
A1  - Takahashi, H
Y1  - 1999/01/01/
N2  - 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.
JF  - Pure and Applied Chemistry
VL  - 71
SN  - 0033-4545
TI  - Synthetic applications of ortho esters
SP  - 415 
AV  - public
EP  -  421
ER  -