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Addition of Diazoalkanes to Enynes Promoted by a Ruthenium Catalyst: Simple Synthesis of Alkenyl Bicyclo[3.1.0]hexane Derivatives

Authors

  • Florian Monnier,

    1. Institut de Chimie de Rennes, UMR 6509, CNRS-Université de Rennes, Organométalliques et Catalyse, Campus de Beaulieu, 35042, Rennes, France, Fax: (+33) 2-2323-6939
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  • Dante Castillo,

    1. Institut de Chimie de Rennes, UMR 6509, CNRS-Université de Rennes, Organométalliques et Catalyse, Campus de Beaulieu, 35042, Rennes, France, Fax: (+33) 2-2323-6939
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  • Sylvie Dérien Dr.,

    1. Institut de Chimie de Rennes, UMR 6509, CNRS-Université de Rennes, Organométalliques et Catalyse, Campus de Beaulieu, 35042, Rennes, France, Fax: (+33) 2-2323-6939
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  • Loïc Toupet Dr.,

    1. Groupe Matière Condensée et Matériaux, UMR 6626, CNRS-Université de Rennes, Campus de Beaulieu, 35042, Rennes, France
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  • Pierre H. Dixneuf Prof.

    1. Institut de Chimie de Rennes, UMR 6509, CNRS-Université de Rennes, Organométalliques et Catalyse, Campus de Beaulieu, 35042, Rennes, France, Fax: (+33) 2-2323-6939
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  • This work was supported by the CNRS and the Ministère de la recherche. The authors are grateful to the latter for a PhD grant to FM and, for additional support, to the European Union through the Cost Program D17, and the Region Bretagne, through a PRIR program (169AOC), and to Institut Universitaire de France for membership (PHD).

Abstract

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[Cp*RuCl(cod)] (Cp*=C5Me5, cod=cyclooctadiene) promotes the reaction of 1,6-enynes with an excess of diazoalkane in dioxane in one step to afford selectively 1-alkenyl bicyclo[3.1.0]hexane derivatives (see scheme, X=O, NTs; Y=CO2Et; R1=H, Me; R2=H; Ts=p-toluenesulfonyl). This novel reaction involves the stereoselective formation of three C[BOND]C bonds and a cyclopropanation step.

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