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Highly Selective Diels-Alder Reactions of Directly Connected Enyne Dienophiles

Mingji Dai, David Sarlah, Maolin Yu, Samuel J. Danishefsky,* Gavin O. Jones and K. N. Houk

*The Sloan-Kettering Institute for Cancer Research Center,1275 York Avenue, Room RRL 1301, New York, New York 10021, Email: s-danishefskyski.mskcc.org

M. Dai, D. Sarlah, M. Yu, S. J. Danishefsky, G. O. Jones, K. N. Houk, J. Am. Chem. Soc., 2007, 129, 645-657.

DOI: 10.1021/ja065762u (free Supporting Information)


Abstract

Cycloadditions of Diels-Alder dienophiles containing linked enyne sites, each substituted with activating groups, occurred specifically at the acetylenic center. A remote acrylyl group bound to the olefinic site totally dominated the regiochemical course of the cycloaddition. Explanations for these findings at the computational level are provided.

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Key Words

Diels-Alder Reaction, Styrenes, Benzoates, Cyclizations


ID: J48-Y2007-0160