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

[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...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2003-11, Vol.42 (44), p.5474-5477
Main Authors: Monnier, Florian, Castillo, Dante, Dérien, Sylvie, Toupet, Loïc, Dixneuf, Pierre H.
Format: Article
Language:English
Subjects:
Catalysis
Chemical Sciences
cyclization
diazo compounds
enynes
heterocycles
Organic chemistry
ruthenium
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Summary:[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C bonds and a cyclopropanation step.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200352477