Straight-chain ω-amino-α,β-unsaturated carbonyl compounds: versatile synthons for the synthesis of nitrogen-containing heterocycles via organocatalytic reactions

Literature Information

Publication Date 2023-11-30
DOI 10.1039/D3QO01734F
Impact Factor 5.281
Authors

Shuhui Li, Xiaoxuan Li, Hui Yao, Mengting Tan, Dan Xu, Nianyu Huang, Nengzhong Wang


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Abstract

Straight-chain ω-amino-α,β-unsaturated carbonyl compounds have been recognized as versatile organic synthons participating in various organocatalytic reactions for the creation of five- and six-membered saturated nitrogen-containing heterocycles, which are important subunits in a broad range of naturally occurring compounds, biologically active molecules, and drugs. Consequently, these organic synthons have attracted significant interest from synthetic and pharmaceutical chemists, and a series of methodologies and strategies have been efficiently developed. In this review, we elaborate and discuss the recent applications of such versatile synthons according to the following organocatalytic reaction modes: (1) covalent catalysis (secondary amine catalysis, phosphine catalysis, and N-heterocyclic carbene catalysis), (2) non-covalent catalysis (Brønsted acid catalysis), and (3) bifunctional catalysis (bifunctional tertiary amine/primary amine catalysis, bifunctional tertiary amine/squaramide catalysis, and bifunctional tertiary amine/thiourea catalysis).

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Source Journal

Organic Chemistry Frontiers

Organic Chemistry Frontiers
CiteScore: 7.8
Self-citation Rate: 8.7%
Articles per Year: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

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