Stereoselective desymmetrisation of prochiral α,α-dicyanoalkenes via domino Michael–Michael addition reactions

Abstract

The desymmetrisation of prochiral α,α-dicyanoalkenes via tandem Michael–Michael addition reactions with α,β-unsaturated ketones catalysed by 9-amino-9-deoxyepicinchona alkaloids was investigated, from which bicyclic products bearing four stereogenic centers were afforded in a single operation with high stereoselectivities (>99% de, up to >99.5% ee).