Organic Chemistry Portal

Abstracts

Search:

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


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.

see article for more examples

see article for more reactions


reaction pathway



Key Words

Diels-Alder Reaction, Styrenes, Benzoates, Cyclizations


ID: J48-Y2007-0160