Lewis Base Activation of Lewis Acids. Vinylogous Aldol Addition Reactions of Conjugated N,O-Silyl Ketene Acetals to Aldehydes

Scott E. Denmark* and John R. Heemstra, Jr.

*Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801, Email: denmarkscs.uiuc.edu

S. E. Denmark, J. R. Heemstra, Jr., J. Am. Chem. Soc., 2006, 128, 1038-1039.

DOI: 10.1021/ja056747c

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Abstract

N,O-Silyl dienyl ketene acetals are useful reagents for highly enantioselective vinylogous aldol additions to various aldehydes in the presence of SiCl₄ and the catalytic action of a chiral phosphoramide. Derivatisations of the morpholine amides are described.

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Key Words

α,β-unsaturated compounds, homoallylic alcohols, Mukayiama Aldol Addition

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ID: J48-Y2006-1360