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Bisoxazolidine-Catalyzed Enantioselective Reformatsky Reaction

Christian Wolf* and Max Moskowitz

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

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

DOI: 10.1021/jo200774e


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.

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Key Words

Reformatsky Reaction, β-Hydroxy Esters

ID: J42-Y2011-2170