Double Asymmetric Induction in Intramolecular C-H Insertion Reactions of α-Diazo β-Keto Esters

Abstract

A new double asymmetric induction in C-C bond formation has been achieved by the use of dirhodium(II) tetrakis[N-phthaloyl-(R) or (S)-phenylalaninate] as a homochiral catalyst in intramolecular C-H insertion of α-diazo β-keto esters of homochiral alcohols. The matched combination of the (+)-neomenthyl esters and the catalyst derived from (R)-phenylalanine produces, after a removal of the ester group, optically active 3-substituted cyclopentanones of up to 80% ee.