Transition metal-catalyzed intermolecular [5+2] and [5+2+1] cycloadditions of allenes and vinylcyclopropanes

Hermann A Wegner; Armin de Meijere; Paul A Wender

doi:10.1021/ja043671w

Transition metal-catalyzed intermolecular [5+2] and [5+2+1] cycloadditions of allenes and vinylcyclopropanes

J Am Chem Soc. 2005 May 11;127(18):6530-1. doi: 10.1021/ja043671w.

Authors

Hermann A Wegner¹, Armin de Meijere, Paul A Wender

Affiliation

¹ Departments of Chemistry and Molecular Pharmacology, Stanford University, Stanford, CA 94305, USA.

PMID: 15869263
DOI: 10.1021/ja043671w

Abstract

Initial examples of the intermolecular Rh(I)-catalyzed [5+2] cycloaddition reaction of bifunctional allenes and vinylcyclopropanes are described. The reactions proceed with facility and in yields of up to 99% with a variety of alkyne-, ester-, styrene-, or cyano-substituents on the allene to afford the corresponding cycloadducts. In the presence of CO, the reaction proceeds to an eight-membered ring cycloadduct and its transannularly closed product, providing the first example of a three-component [5+2+1] cycloaddition with allenes.