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

Org Lett

Department of Process Research, Merck & Co., Inc., P.O. Box 2000, Rahway, New Jersey 07065, USA.

Published: February 2004

[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.

Download full-text PDF

Source
http://dx.doi.org/10.1021/ol036380lDOI Listing

Publication Analysis

Top Keywords

benzylic alcohols
8
stereoselective carbon-carbon
4
carbon-carbon bond
4
bond formation
4
formation mitsunobu
4
mitsunobu displacement
4
displacement chiral
4
chiral secondary
4
secondary benzylic
4
alcohols [reaction
4

Similar Publications

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!