Issue 8, 2024

Palladium-catalyzed asymmetric [4 + 3] cycloaddition of acyclic α,β-unsaturated imines with trimethylenemethane donors: access to chiral non-fused azepines

Abstract

We report herein a Pd-catalyzed asymmetric [4 + 3] cycloaddition of acyclic α,β-unsaturated imines with trimethylenemethane (TMM) donors under mild conditions. A variety of non-fused azepines are obtained in good yields (up to 90% yield) with high enantioselectivity (up to 97% ee). The reaction features a broad substrate scope and good functional group tolerance, and the cyano-, benzoyl-, and amino-TMM donors are all suitable for this cycloaddition.

Graphical abstract: Palladium-catalyzed asymmetric [4 + 3] cycloaddition of acyclic α,β-unsaturated imines with trimethylenemethane donors: access to chiral non-fused azepines

Supplementary files

Article information

Article type
Research Article
Submitted
11 Jan 2024
Accepted
27 Feb 2024
First published
28 Feb 2024

Org. Chem. Front., 2024,11, 2326-2331

Palladium-catalyzed asymmetric [4 + 3] cycloaddition of acyclic α,β-unsaturated imines with trimethylenemethane donors: access to chiral non-fused azepines

T. Li, S. Su, J. Shen, M. Zang, Y. Liu, Q. Wang and W. Deng, Org. Chem. Front., 2024, 11, 2326 DOI: 10.1039/D4QO00064A

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