Accessible sugars as asymmetric olefin epoxidation organocatalysts: glucosaminide ketones in the synthesis of terminal epoxides

O Boutureira, JF McGouran, RL Stafford…

Index: Boutureira, Omar; McGouran, Joanna F.; Stafford, Robert L.; Emmerson, Daniel P. G.; Davis, Benjamin G. Organic and Biomolecular Chemistry, 2009 , vol. 7, # 20 p. 4285 - 4288

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Citation Number: 16

Abstract

A systematically varied series of conformationally restricted ketones, readily prepared from N- acetyl-D-glucosamine, were tested against representative olefins as asymmetric epoxidation catalysts showing useful selectivities against terminal olefins and, in particular, typically difficult 2, 2-disubstituted terminal olefins.