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

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journal contribution
posted on 21.08.2008, 00:00 by Bin Tan, Zugui Shi, Pei Juan Chua, Guofu Zhong
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.