A copper-catalyzed method for the facially selective addition of grignard reagents to cyclopropenes.
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 generated can be reacted with electrophiles to produce highly functionalized cyclopropanes.
Liao
Lian-An
LA
Brown Laboratories, Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, USA.
Fox
Joseph M
JM