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Highly Enantioselective, Catalytic Conjugate Addition of Cyanide to α,β-Unsaturated Imides

Glenn M. Sammis and Eric N. Jacobsen*

*Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, Email: jacobsenchemistry.harvard.edu

G. M. Sammis, E. N. Jacobsen, J. Am. Chem. Soc., 2003, 125, 4442-4443.

DOI: 10.1021/ja034635k (free Supporting Information)


Abstract

A (Salen)Al-Cl complex catalyzes the asymmetric conjugate addition of hydrogen cyanide to α,β-unsaturated imides in high yields and enantioselectivities. The cyanide adducts can readily be converted into a variety of useful chiral building blocks, including α-substituted-β-amino acids.

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Key Words

Nitriles, Conjugate Addition


ID: J48-Y2003-1420