4.5 Review

Recent Advancement on the Organocatalyzed Asymmetric Conjugate Addition using Maleimide as a Potential Substrate

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WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.202300387

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Maleimide; organocatalysis; asymmetric conjugate addition; Michael addition; nitrogen heterocycles

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This article summarizes the progress made in the past 10 years in using unprotected and protected maleimides for asymmetric organocatalytic 1,4-conjugate additions. The review provides an overview of different types of nucleophiles, catalysts, substrate scope, limitations, mechanism, and synthetic utilities for each reaction. It encourages researchers worldwide to focus on the development of new methodologies, including asymmetric photo redox catalysis, for the further functionalization of maleimides.
Asymmetric organocatalytic 1,4-conjugate addition is considered as an effective, powerful and sustainable method for carbon-carbon bond formation. The core structure of maleimides or succinimides were found in several bioactive molecules as well as in natural products. Unprotected and protected maleimides were employed as an electrophile to construct novel succinimide based organic molecules. The rapid development of several new effective and prominent methodologies encourages us to write a review by summarizing the recent updates. In this review, we present an overview of the past 10 years progress on the asymmetric organocatalytic 1,4 conjugate additions using unprotected and protected maleimides. Special attention has been paid classifying the types of nucleophiles as well as catalysts employed for this asymmetric transformation along with substrate scope, limitation, mechanism, and synthetic utilities for each reaction. Knowing the versatility of maleimides, this review will encourage active researchers around the globe to put more efforts on the development of new methodologies including asymmetric photo redox catalysis for further functionalization of maleimides. The use of unprotected and protected maleimides as electrophiles was employed to synthesize new succinimide-based organic molecules using several catalytic approaches. In this review, we present an overview of the past 10 years progress on the asymmetric organocatalytic conjugate additions of maleimides.image

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