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