Asymmetric Induction in 1,3-Dipolar Cycloaddition of Diazofluorene with Menthyl or 8-Phenylmenthyl Acrylate and Fumarate Derivatives

Article abstract of DOI:10.1246/cl.1987.93

Optical yields in the 1,3-dipolar cycloaddition of diazofluorene with chiral acrylate or fumarate derivatives were found to be considerably improved by use of Corey's 8-phenylmenthyl group as a chiral O-alkyl group in these esters.The absolute stereochemistry of resulting cyclopropanes is different from the one expected from the "diazo-exchange" mechanism proposed by Walborsky et al.