The Journal of Organic Chemistry

Highly enantioselective intramolecular cyclopropanation reactions of N-Allylic-N-methyldiazoacetamides catalyzed by chiral dirhodium (II) carboxamidates

MP Doyle, AV Kalinin

Index: Doyle, Michael P.; Kalinin, Alexey V. Journal of Organic Chemistry, 1996 , vol. 61, # 6 p. 2179 - 2184

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Citation Number: 71

Abstract

Catalytic diazo decomposition of representative N-allylic-N-methyldiazoacetamides produced the corresponding intramolecular cyclopropanation products in good to excellent yields and with exceptional enantiocontrol. In the simplest case, with N-allyl-N- methyldiazoacetamide, catalysis by dirhodium (II) tetrakis [methyl 2-oxapyrrolidine-5 (S)- carboxylate], Rh2 (5 (S)-MEPY) 4, achieved the highest yield and enantioselectivity (93% ...