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Short Paper | Regular issue | Vol 94, No. 3, 2017, pp.541-553
Published online, 17th March, 2017
DOI: 10.3987/COM-17-13656
Catalytic Asymmetric Intramolecular Cyclopropanation of α-Diazo-α-phosphoryl Acetate

Saori Inoue, Kotaro Nagatani, Yunosuke Hoshino, Haruka Tezuka, and Masahisa Nakada*

*Department of Chemistry and Biochemistry, Faculty of Science and Engineering, Waseda University, 3-4-1 Ohkubo, Shinjuku-ku, Tokyo 169-8555, Japan

Abstract

The catalytic asymmetric intramolecular cyclopropanation (CAIMCP) of α-diazo-α-diphenylphosphoryl acetate has been investigated. The maximum ee of the CAIMCP was 91% and the absolute configuration of the two products was successfully determined. Our previously reported model to explain the enantiofacial selectivity of the reacting alkene was successfully applied to rationalize the enantioselectivity of the CAIMCP.