Anti-selective and regioselective aldol addition of ketones with aldehydes using MgI 2 as promoter

HX Wei, RL Jasoni, H Shao, J Hu, PW Paré

Index: Wei, Han-Xun; Jasoni, Richard L.; Shao, Huawu; Hu, Jiali; Pare, Paul W. Tetrahedron, 2004 , vol. 60, # 51 p. 11829 - 11835

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Citation Number: 32

Abstract

The first example of a direct aldehyde–ketone coupling using the secondary amine piperidine as base in the presence of MgI2 to generate high selectivity of anti-aldol products from unmodified ethyl ketones in high yield is reported. The coupling reactions were carried out in a one-pot reaction by mixing four reaction components at room temperature. In the case of unsymmetrical ketones, addition was made to the less hindered α-side.