Enantioselective Synthesis of Cyclopropanes Bearing Geminal Carboxy Groups

Significance

The authors report a variation on the classic rhodium-catalyzed cyclopropanation of alkenes with diazo compounds. Chiral cyclopropanes bearing two carboxy groups are a challenging target since the control of enantioselectivity is difficult. The authors obtain these targets in high enantioselectivity and good yields by utilizing α-amido-α-diazoacetate derivatives (1).

Book: M. P. Doyle, M. A. McKervey, T. Ye Modern Catalytic Methods for Organic Synthesis with ­Diazo Compounds: From Cyclopropanes to Ylides; Wiley-VCH: New York, 1998.