Issue 1, 2024

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

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).

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

Article information

Article type
Review Article
Submitted
20 10 2023
Accepted
21 11 2023
First published
30 11 2023

Org. Chem. Front., 2024,11, 236-253

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

S. Li, X. Li, H. Yao, M. Tan, D. Xu, N. Huang and N. Wang, Org. Chem. Front., 2024, 11, 236 DOI: 10.1039/D3QO01734F

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