Stereoselective Carbon−Carbon Bond Formation via the Mitsunobu Displacement of Chiral Secondary Benzylic Alcohols

Autor: Hillier, M. C., Desrosiers, J.-N., Marcoux, J.-F., Grabowski, E. J. J.
Zdroj: Organic Letters; February 2004, Vol. 6 Issue: 4 p573-576, 4p
Abstrakt: The stereoselective displacement of a variety of chiral benzylic alcohols with triethylmethanetricarboxylate (TEMT) under Mitsunobu conditions (DEAD, PMe3) has been demonstrated to proceed in good yield (70−94%) and with a high degree of inversion. Subsequent saponification and decarboxylation of the products thus obtained provide chiral 3-aryl-3-substituted propanoic acids without racemization.
Databáze: Supplemental Index