Enantioselective Michael Addition to α,β-Unsaturated Imides Catalyzed by a Bifunctional Organocatalyst


  • This work was supported by grants from the 21st Century COE Program “Knowledge Information Infrastructure for Genome Science” and KAKENHI (16390006).


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High enantioselectivities (up to 94 % ee) were attained in the Michael addition of a variety of α,β-unsaturated imides 1 and malononitrile (2) catalyzed by bifunctional thiourea 4. The pyrrolidinone moiety of 1 plays a key role in the reaction. The reaction provides access to a variety of Michael adducts 3 (see scheme; R=aryl and alkyl groups).