Stereoselective carbon-carbon bond formation via the Mitsunobu displacement of chiral secondary benzylic alcohols

Org Lett. 2004 Feb 19;6(4):573-6. doi: 10.1021/ol036380l.

Abstract

[reaction: see text] The stereoselective displacement of a variety of chiral benzylic alcohols with triethylmethanetricarboxylate (TEMT) under Mitsunobu conditions (DEAD, PMe(3)) 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.