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Communication | Regular issue | Vol 81, No. 5, 2010, pp.1149-1155
Published online, 11th March, 2010
DOI: 10.3987/COM-10-11930
Asymmetric Intermolecular N-H Insertion Reaction of Phenyldiazoacetates with Anilines Catalyzed by Achiral Dirhodium(II) Carboxylates and Cinchona Alkaloids

Hiroaki Saito,* Taketo Uchiyama, Muneharu Miyake, Masahiro Anada, Shunichi Hashimoto, Tohru Takabatake, and Shinichi Miyairi

*School of Pharmacy, Nihon University, 7-7-1 Narashinodai, Funabashi-shi, Chiba 274-8555, Japan

Abstract

Asymmetric N–H insertion of phenyldiazoacetates with anilines catalyzed cooperatively by achiral dirhodium(II) carboxylates and cinchona alkaloids is described. A new catalytic system of dirhodium(II) tetrakis(triphenylacetate), Rh2(TPA)4, and dihydrocinchonine provides phenylglycine derivatives in up to 71% ee.