Lewis Base Activation of Lewis Acids. Vinylogous Aldol Reactions

Scott E. Denmark* and Gregory L. Beutner

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

S. E. Denmark, G. L. Beutner, J. Am. Chem. Soc., 2003, 125, 7800-7801.

DOI: 10.1021/ja035448p

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Abstract

A highly regioselective vinylogous aldol reaction provides δ-hydroxy enones for a variety of aldehyde and dienol ether structures in good yields, excellent enantioselectivities, and in some cases excellent anti diastereoselectivities in the presence of SiCl₄ and the catalytic action of a chiral phosphoramide.

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Key Words

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

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ID: J48-Y2003-1520