An Efficient and Scalable One-Pot Double Michael Addition-Dieckmann Condensation for the Synthesis of 4,4-Disubstituted Cyclohexane β-Keto Esters
The Journal of Organic Chemistry2007Vol. 72(19), pp. 7455–7458
Citations Over Time
Michael DeGraffenreid, Sarah M. Bennett, Sébastien Caillé, Felix González-López de Turiso, Randall W. Hungate, Lisa D. Julian, Jacob A. Kaizerman, Dustin L. McMinn, Yosup Rew, Daqing Sun, Xuelei Yan, Jay P. Powers
Abstract
A simple, scalable, and efficient one-pot methodology for the synthesis of 4,4-disubstituted cyclohexane beta-keto esters from benzylic nitriles or esters and methyl acrylate promoted by potassium tert-butoxide is described. The process relies on a tandem double Michael addition-Dieckmann condensation reaction, which results in the formation of three discrete carbon-carbon bonds in a single pot, including a quaternary center. The method allows for the convenient and rapid synthesis of a variety of 4-aryl-4-cyano-2-carbomethoxycyclohexanone and 4-aryl-2,4-biscarbomethoxycyclohexanone building blocks for use in natural products synthesis and medicinal chemistry.
Related Papers
- → Control of the Regio‐ and Diastereoselectivity for the Preparation of Highly Functionalized Terpenic Cyclopentanes through Radical Cyclization(2011)10 cited
- → A stereocontrolled synthesis of trisubstituted cyclohexanes and cyclopentanes. Its application to the synthesis of 11-deoxyprostaglandins.(1989)15 cited
- → Palladium-Catalyzed Synthesis of Spirocyclic Cyclopentanes(2007)
- → Palladium-Catalyzed Enyne Cyclization towards Complex Cyclopentanes(2011)
- → ChemInform Abstract: Synthesis of Functionalised Cyclopentanes by Intramolecular Radical‐mediated Cyclisations of Terminal Allenic Ketones.(1986)