Selective Ruthenium-Catalyzed Transformations of Enynes with Diazoalkanes into Alkenylbicyclo[3.1.0]hexanes

Florian Monnier, Chloé Vovard-Le Bray, Dante Castillo, Vincent Aubert, Sylvie Dérien, Pierre H. Dixneuf,* Loic Toupet, Andrea Ienco and Carlo Mealli

*Laboratoire "catalyse et organométalliques", Institut Sciences Chimiques de Rennes, UMR 6226 CNRS-Université de Rennes 1, 35042 Rennes Cedex, France, Email: pierre.dixneufuniv-rennes1.fr

F. Monnier, C. Vovard-Le Bray, D. Castillo, V. Aubert, S. Dérien, P. H. Dixneuf, L. Toupet, A. Ienco, C. Mealli, J. Am. Chem. Soc., 2007, 129, 6037-6049.

DOI: 10.1021/ja0700146

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Abstract

The reaction of various 1,6-enynes with N₂CHSiMe₃ in the presence of RuCl(COD)Cp* as catalyst precursor leads to the general formation of alkenylbicyclo[3.1.0]hexanes at room temperature in good yield with high stereoselectivity. The catalytic formation of alkenylbicyclo[3.1.0]hexanes also takes place in the presence of N₂CHCO₂Et or N₂CHPh.

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Key Words

Cyclopropanes, Pyrrolidines, Tetrahydrofurans, Cyclopentanes

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ID: J48-Y2007-1630