Organic Chemistry Portal



Lewis Base Catalyzed Additions of Silyl Ketene Imines to Aldehydes

Scott E. Denmark,* Tyler W. Wilson, Matthew T. Burk and John R. Heemstra, Jr.

*Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801, Email:

S. E. Denmark, T. W. Wilson, M. T. Burk, J. R. Heemstra, Jr., J. Am. Chem. Soc., 2007, 129, 14864-14865.

DOI: 10.1021/ja077134y


In the presence of SiCl4 and a catalytic amount of a chiral phosphoramide, silyl ketene imines undergo extremely rapid and high yielding addition to a wide variety of aromatic aldehydes with excellent diastereo- and enantioselectivity. The nitrile function serves as a useful precursor for further synthetic manipulation.

see article for more examples

Key Words


ID: J48-Y2007-3880