Addition of Diazoalkanes to Enynes Promoted by a Ruthenium Catalyst: Simple Synthesis of Alkenyl Bicyclo[3.1.0]hexane Derivatives - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Angewandte Chemie International Edition Année : 2003

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

Résumé

[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 CC bonds and a cyclopropanation step.

Dates et versions

hal-00164248 , version 1 (19-07-2007)

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Citer

Florian Monnier, Dante Castillo, Sylvie Dérien, Loic Toupet, Pierre H. Dixneuf. Addition of Diazoalkanes to Enynes Promoted by a Ruthenium Catalyst: Simple Synthesis of Alkenyl Bicyclo[3.1.0]hexane Derivatives. Angewandte Chemie International Edition, 2003, 42 (44), pp.5474 - 5477. ⟨10.1002/anie.200352477⟩. ⟨hal-00164248⟩
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