Journal of the American Chemical Society

A copper-catalyzed method for the facially selective addition of Grignard reagents to cyclopropenes

L Liao, JM Fox

Index: Liao, Lian-An; Fox, Joseph M. Journal of the American Chemical Society, 2002 , vol. 124, # 48 p. 14322 - 14323

Full Text: HTML

Citation Number: 69

Abstract

A Cu-catalyzed method for the addition of Grignard reagents to 1-alkyl-3- hydroxymethylcyclopropenes and their MOM ethers is described. The face of addition is syn relative to the hydroxymethyl and alkoxymethyl groups. Excellent diastereoselectivity is observed for a range of alkyl, alkenyl, and alkynylmagnesium halides. The addition reactions create chiral all-carbon quaternary centers, and the cyclopropylmetals that are ...