Issue 19, 2024

Advances in organocatalytic asymmetric [3 + 3] cycloadditions: synthesis of chiral six-membered (hetero)cyclic compounds

Abstract

Organocatalytic asymmetric [3 + 3] cycloaddition underpins the efficient synthesis of chiral six-membered (hetero)cyclic compounds. Various elegant works were exploited to promote the prosperity of this cycloaddition-based methodology in past decades. The advantage of this unique strategy lies in great compatibility with flexible catalytic modes and multiple three-atom building blocks. This review summarizes the development of organocatalytic asymmetric [3 + 3] cycloaddition over the past twenty years. Both mechanistic studies and the activation mode of various organocatalytic systems, including (1) chiral amine catalysis, (2) chiral bifunctional catalyst catalysis, (3) chiral N-heterocyclic carbene catalysis, (4) chiral phosphoric acid catalysis, and (5) other asymmetric organocatalysis (isothioureas, phosphine and cooperative catalysis) are discussed in this review. Additionally, for each catalytic pattern, three-atom building blocks for organocatalytic asymmetric [3 + 3] cycloaddition were classified as all-carbon three-atom, aza-three-atom, oxa-three-atom building blocks and those containing other heteroatoms. This review has not only given a systematic summary of this topic, but also provided insights into the remaining challenges, which will promote the future development of this field.

Graphical abstract: Advances in organocatalytic asymmetric [3 + 3] cycloadditions: synthesis of chiral six-membered (hetero)cyclic compounds

Article information

Article type
Review Article
Submitted
20 Mar 2024
Accepted
01 May 2024
First published
01 May 2024

Org. Chem. Front., 2024,11, 5573-5604

Advances in organocatalytic asymmetric [3 + 3] cycloadditions: synthesis of chiral six-membered (hetero)cyclic compounds

Z. Zhu, T. Li, S. Liu and F. Shi, Org. Chem. Front., 2024, 11, 5573 DOI: 10.1039/D4QO00515E

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