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Anti-selective and regioselective aldol addition of ketones with aldehydes using MgI2 as promoter

Han-Xun Wei*, Richard L. Jasoni, Huawu Shao, Jiali Hu and Paul W. Paré

*Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX 79409, USA, Email: hweirdg.boehringer-ingelheim.com

H.-X. Wei, R. L. Jasoni, H. Shao, J. Hu, P. W. Pare, Tetrahedron, 2004, 60, 11829-11835.

DOI: 10.1016/j.tet.2004.09.098


 

Abstract

A one-pot aldehyde-ketone coupling using the secondary amine piperidine in the presence of MgI2 gave anti-aldol products from unmodified ethyl ketones in high yields. In the case of unsymmetrical ketones, addition was made to the less hindered α-side.

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Key Words

Piperidine, Aldol reaction, Magnesium iodide, Ethyl ketone


ID: J72-Y2004-1140