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

Abstract

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.

A C–H functionalization approach to diverse nitrogenous scaffolds through conjugate addition of catalytic allyliron nucleophiles

“…1,3 Conjugate addition of carbon nucleophiles (Michael addition) to the readily available maleimide scaffold constitutes a straightforward and attractive route for quickly accessing 3-alkylated succinimides. [8][9][10][11] However, there is a distinct lack of suitable nucleophiles for the C]C bond allylation of maleimide derivatives. Common organometallic allyl nucleophiles such as magnesium, 12 silicon, 13 boron, 14 indium, 15 and tin 16 reagents all selectively provide the 1,2-adduct of direct carbonyl addition, rather than 3-allylated succinimide derivative resulting from 1,4-addition.…”