Issue 21, 2021

Generation of azolium dienolates as versatile nucleophilic synthons via N-heterocyclic carbene catalysis

Abstract

N-Heterocyclic carbene (NHC) organocatalysis has emerged as a powerful tool in the field of modern organic synthesis especially in asymmetric construction of various cyclic skeletons. As emerging NHC-bound nucleophilic intermediates, azolium dienolates have been widely investigated and applied in NHC-catalyzed transformations due to their unique reactivities and versatile structures. Particularly, four representative kinds of reactive azolium dienolates (I–IV) have been explored as versatile nucleophilic synthons via either α-functinalization or remote γ-functionalization to achieve efficient construction of complex skeletons. Moreover, these NHC-bound intermediates had wide-ranging applications in asymmetric synthesis of diversely enantioenriched centrally chiral molecules. In this review, the recent advances in NHC-catalyzed generation of azolium dienolates from different precursors and their applications in the synthesis of various valuable molecules are summarized comprehensively.

Graphical abstract: Generation of azolium dienolates as versatile nucleophilic synthons via N-heterocyclic carbene catalysis

Article information

Article type
Review Article
Submitted
30 Jul 2021
Accepted
31 Aug 2021
First published
01 Sep 2021

Org. Chem. Front., 2021,8, 6138-6166

Generation of azolium dienolates as versatile nucleophilic synthons via N-heterocyclic carbene catalysis

J. Gao, J. Feng and D. Du, Org. Chem. Front., 2021, 8, 6138 DOI: 10.1039/D1QO01127H

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