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Enyne Cross-Metathesis with Strained, Geminally-Substituted Alkenes: Direct Access to Highly Substituted 1,3-Dienes

Daniel A. Clark, Brenda S. Basile, William S. Karnofel and Steven T. Diver*

*Department of Chemistry, University at Buffalo, The State University of New York, Amherst, New York 14260, Email: diverbuffalo.edu

D. A. Clark, B. S. Basile, W. S. Karnofel, S. T. Diver, Org. Lett., 2008, 10, 4927-4929.

DOI: 10.1021/ol802007q (free Supporting Information)


Abstract

Angle strain in methylene cyclobutane drives a cross-enyne metathesis with 1-alkynes, giving 1,1,3-trisubstituted 1,3-dienes in good isolated yields. An extensive survey of Grubbs’ second-generation catalysts led to optimized reaction conditions.

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Key Words

Enyne Metathesis, Cyclobutanes


ID: J54-Y2008-3280