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

Abstract

[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. Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2003/z52477_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.