Control of Four Stereocenters in an Organocatalytic Domino Double Michael Reaction: Efficient Synthesis of Multisubstituted Cyclopentanes

A highly enantioselective and diastereoselective domino organocatalytic double Michael reaction which provides expedited access to multifunctionalized five-membered rings catalyzed by 9-amino-9-deoxyepiquinine (V) has been developed. Simple operational procedures, high yields (81−92%), excellent enantioselectivity (90−97% ee), diastereoselectivities (95:5−>99:1 dr), and immense potential of synthetic versatility of the products render this new methodology highly appealing for asymmetric synthesis.