Asymmetric Diels–Alder reaction involving chiral benzimidazoles as organocatalysts

Recent progress in asymmetric organocatalysis has led to the development of several asymmetric transformations that employ various substrates. Among these substrates, maleimides have emerged as excellent Michael acceptors, dienophiles, and dipolarophiles. In this Focus Review we highlight the advances in the asymmetric synthesis of succinimide derivatives through asymmetric organocatalytic addition reactions of maleimides.

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Stereoselective Intramolecular Dearomatizative [4+2] Cycloaddition of Linked Ethynylnaphthol–Benzofuran Systems

Beppu

Arae

Furusawa

et al. 2017

Eur J Org Chem

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A base‐catalyzed stereoselective intramolecular dearomatizative [4+2] cycloaddition of o‐phenylene‐linked ethynylnaphthol–benzofuran systems was explored. In this reaction, we presume the involvement of electrophilic vinylidene o‐quinone methides (4π), which add across the electron‐rich furan double bonds (2π) to produce elaborate, fused oxa‐polyheterocyclic frameworks with consecutive quaternary and tertiary asymmetric carbon atoms as single diastereomers. The catalytic and enantioselective synthesis of these chiral fused polyheterocyclic structures is also feasible with the use of a prevalent cinchonidine or cinchonine chiral base.

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Asymmetric Diels–Alder reaction involving chiral benzimidazoles as organocatalysts

Abstract: (S)-(-)-2-(α-hydroxyethyl)-benzimidazole and (S)-(+)-2-(α-hydroxybenzyl)-benzimidazole work as chiral Brønsted bases (BBs) in Diels-Alder reaction between anthrone and maleimides under mild reaction condition. These chiral BBs cause asymmetric induction.

Cited by 9 publications

References 26 publications

Addition Reactions: Cycloaddition

Addition Reactions: Cycloaddition

Asymmetric Organocatalytic Addition Reactions of Maleimides: A Promising Approach Towards the Synthesis of Chiral Succinimide Derivatives

Stereoselective Intramolecular Dearomatizative [4+2] Cycloaddition of Linked Ethynylnaphthol–Benzofuran Systems

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