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Halocycloalkenones as Diels-Alder Dienophiles. Applications to Generating Useful Structural Patterns

Audrey G. Ross, Steven D. Townsend and Samuel J. Danishefsky*

*Department of Chemistry, Columbia University, Havemeyer Hall, 3000 Broadway, New York, New York 10027, United States, Email: s-danishefskyski.mskcc.org

A. G. Ross, S. D. Townsend, S. J. Danishefsky, J. Org. Chem., 2013, 78, 204-210.

DOI: 10.1021/jo302230m (free Supporting Information)


Abstract

Halocycloalkenones are potent dienophiles in Diels-Alder cycloadditions. 2-Brominated cycloalkenone dienophiles are highly endo selective and significantly more reactive than their nonhalogenated parent compounds. A base-mediated reaction enables the facile conversion of brominated cyclobutanone Diels-Alder adducts to synthetically useful cyclopropyl derivatives.

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Key Words

Diels-Alder reaction, Favorskii Reaction, Cyclobutanones, Cyclopropanes


ID: J42-Y2013-0040