Organic Chemistry Portal

Abstracts

Search:

Bisoxazolidine-Catalyzed Enantioselective Reformatsky Reaction

Christian Wolf* and Max Moskowitz

*Department of Chemistry, Georgetown University, Washington, D.C. 20057, United States, Email: cw27georgetown.edu

C. Wolf, M. Moskowitz, J. Org. Chem., 2011, 76, 6372-6376.

DOI: 10.1021/jo200774e (free Supporting Information)


Abstract

A readily available chiral bisoxazolidine catalyzes the asymmetric Reformatsky reaction between ethyl iodoacetate and aromatic aldehydes to yield 3-hydroxy-3-(4-aryl)propanoates in high yields and good enantioselectivities in the presence of dimethylzinc and air at room temperature within 1 h. In contrast to aromatic substrates, relatively low ee’s are obtained with aliphatic aldehydes.

see article for more examples



Key Words

Reformatsky Reaction, β-Hydroxy Esters


ID: J42-Y2011-2170