 The activation of saturated ester a-carbon as enolate is one of the most versatile strategies in organic synthesis. However, similar activation of the typically inert ester �-carbon of the saturated ester as nucleophile has remained a challenge and largely undeveloped with limited studies based on transition-metal catalysis. Herein we report the first direct organocatalytic NHC-catalyzed activation of simple saturated ester �-carbon as nucleophile. The catalytically generated nucleophilic ester �-carbon reacted in highly stereoselective manner with various electrophiles such as enones, ketones and imines.

Toward new activation modes with N-heterocyclic carbene catalysis: Activation of ester β-carbons as nucleophiles

245th National Meeting (2013)

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