Facially selective and regioselective carbometalation of cyclopropenes by aryl Grignard reagents.
Described is a Cu-catalyzed methodology for adding aryl Grignard reagents to 3-hydroxymethylcyclopropene derivatives with high regio- and diastereoselectivity. The cyclopropylmetals can be trapped with a variety of electrophiles to generate highly substituted cyclopropanes.
Yan
Ni
N
Brown Laboratories, Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, USA.
Liu
Xiaozhong
X
Fox
Joseph M
JM
D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003521:Cyclopropanes / Q000737:chemistry*; D007454:Iodides / Q000737:chemistry*; D008968:Molecular Conformation; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism
C527429:3-hydroxymethylcyclopropene; D003521:Cyclopropanes; D007454:Iodides; D009942:Organometallic Compounds; D003300:Copper; C073870:cuprous iodide