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Crossed aldol reaction using cross-linked polymer-bound lithium dialkylamide

Atsushi Seki, Fusae Ishiwata, Youichi Takizawa and Masatoshi Asami*

*Department of Advanced Materials Chemistry, Graduate School of Engineering, Yokohama National University, 79-5 Tokiwadai, Hodogaya-ku, Yokohama 240-8501, Japan, Email:

A. Seki, F. Ishiwata, Y. Takizawa, M. Asami, Tetrahedron, 2004, 60, 5001-5011.

DOI: 10.1016/j.tet.2004.04.026


Reusable polymer-bound lithium dialkylamides were employed in crossed aldol reaction of various carbonyl compounds with aldehydes to afford the corresponding β-hydroxycarbonyl compounds. The introduction of spacer chains between the base moiety and the polystyrene backbone increased the yields of the desired aldol adducts.

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Key Words

Supported reagents, Lithium dialkylamides, Aldol reaction, Aldol-Addition, β-Hydroxycarbonyl compounds, β-Hydroxycarboxylic compounds, Deprotonation, Lithium enolates

ID: J72-Y2004-480