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Overriding Felkin Control: A General Method for Highly Diastereoselective Chelation-Controlled Additions to α-Silyloxy Aldehydes

Gretchen R. Stanton, Corinne N. Johnson and Patrick J. Walsh*

*P. Roy and Diana T. Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, Email:

G. R. Stanton, C. N. Johnson, P. J. Walsh, J. Am. Chem. Soc., 2010, 132, 4399-4408.

DOI: 10.1021/ja910717p

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Usually, silyl-protected α-hydroxy aldehydes undergo Felkin addition due to steric and eletronic properties of the silyl group. However, dialkylzincs, functionalized dialkylzincs, and vinylzinc reagents add to silyl-protected α-hydroxy aldehydes with high selectivity for chelation-controlled or anti-Felkin products in the presence of alkylzinc halides or triflates.

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ID: J48-Y2010-0660