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An Efficient and Scalable One-Pot Double Michael Addition-Dieckmann Condensation for the Synthesis of 4,4-Disubstituted Cyclohexane β-Keto Esters

Michael R. DeGraffenreid, Sarah Bennett, Sebastien Caille, Felix Gonzalez-Lopez de Turiso, Randall W. Hungate, Lisa D. Julian,* Jacob A. Kaizerman, Dustin L. McMinn, Yosup Rew, Daqing Sun, Xuelei Yan and Jay P. Powers

*Department of Medicinal Chemistry, Amgen Incorporated, 1120 Veterans Boulevard, South San Francisco, California 94080, Email: ljulianamgen.com

M. R. DeGraffenreid, S. Bennett, S. Caille, F. Gonzalez-Lopez de Turiso, R. W. Hungate, L. D. Julian, J. A. Kaizerman, D. L. McMinn, D. Sun, X. Yan, J. P. Powers, J. Org. Chem., 2007, 72, 7455-7458.

DOI: 10.1021/jo071202h (free Supporting Information)


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Abstract

A simple, scalable, and efficient one-pot methodology for the synthesis of 4,4-disubstituted cyclohexane β-keto esters from benzylic nitriles or esters and methyl acrylate relies on a tandem double Michael addition-Dieckmann condensation reaction promoted by potassium tert-butoxide, which results in the formation of three discrete carbon-carbon bonds in a single pot, including a quaternary center.


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Key Words

Diekmann Condensation, Michael Addition, Cyclohexanones


ID: J42-Y2007-2960