The desymmetrisation of prochiral alpha,alpha-dicyanoalkenes via tandem Michael-Michael addition reactions with alpha,beta-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).