Organic Chemistry Portal

Abstracts

Search:

Copper Catalyzed Asymmetric Synthesis of Chiral Allylic Esters

Koen Geurts, Stephen P. Fletcher and Ben L. Feringa*

*Department of Organic Chemistry and Molecular Inorganic Chemistry, Stratingh Institute, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands, Email: B.L.Feringarug.nl

K. Geurts, S. P. Fletcher, B. L. Feringa, J. Am. Chem. Soc., 2006, 128, 15572-15573.

DOI: 10.1021/ja065780b (free Supporting Information)


see article for more reactions

Abstract

A chemo- and regioselective, Cu-catalyzed asymmetric addition of Grignard reagents to 3-bromopropenyl esters provides allylic esters in high yields and enantioselectivities using Taniaphos as ligand. The method is a practical route to chiral, nonracemic allylic alcohols.

see article for more examples



Synthesis of Optically Active Bifunctional Building Blocks through Enantioselective Copper-Catalyzed Allylic Alkylation Using Grignard Reagents

A. W. van Zijl, F. López, A. J. Minnaard, B. L. Feringa, J. Org. Chem., 2007, 72, 2558-2563.


Key Words

allylic alcohols, allylation


ID: J48-Y2006-4000