Organocatalytic Michael addition of cyclopentane-1,2-dione to different electophiles has been investigated. Cyclopentane-1,2-dione undergoes organocatalytic reaction with nitroolefins giving 3-substituted products in excellent yield (up to 97%) and good stereoselectivity (up to 76% ee). Furthermore, cyclopenta-1,2-dione also goes a organocatalytic cascade Michael addition/hemiacetalisation reaction with �,?-unsaturated a-ketoesters giving a bicyclic product in excellent yield (up to 89%) and stereoselectivity (up to 98% ee). Scheme 1: Michael addition to cyclopentane-1,2-dione

Enantioselective organocatalytic Michael addition of cyclopentane-1,2-diones to electrophiles

248th National Meeting (2014)

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