Diastereoselective synthesis of benzazocines by Zn(OTf)2-catalyzed (4+4) cyclocondensation of multisubstituted donor–acceptor cyclopropanes with anthranils

Xuelian Huang; Gaosheng Yang; Zhuo Chai

doi:10.1039/D4CC06690A

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Diastereoselective synthesis of benzazocines by Zn(OTf)₂-catalyzed (4+4) cyclocondensation of multisubstituted donor–acceptor cyclopropanes with anthranils†

Xuelian Huang,^a Gaosheng Yang

*^a and Zhuo Chai

*^a

Author affiliations

* Corresponding authors

^a MOE Key Laboratory of Functional Molecular Solids, Anhui Laboratory of Molecule-Based Materials, Institute of Organic Chemistry, College of Chemistry and Materials Science, Anhui Normal University, 189 South Jiuhua Road, Wuhu, Anhui 241002, China
E-mail: gshyang@mail.ahnu.edu.cn, chaizhuo@ahnu.edu.cn

Abstract

A Zn(OTf)₂-catalyzed (4+4) cyclocondensation of anthranils with 2-(trans-1-aroyl-2-arylcyclopropyl)malonates delivers a range of polycyclic benzazocines featuring an oxa-bridged eight-membered ring in excellent yields and with exclusive diastereoselectivity. Further synthetic manipulations of these products enable rapid access to diverse useful heterocyclic molecular scaffolds.

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Article information

DOI: https://doi.org/10.1039/D4CC06690A
Article type: Communication
Submitted: 23 Dec 2024
Accepted: 31 Jan 2025
First published: 03 Feb 2025

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Chem. Commun., 2025,61, 3704-3707

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Diastereoselective synthesis of benzazocines by Zn(OTf)₂-catalyzed (4+4) cyclocondensation of multisubstituted donor–acceptor cyclopropanes with anthranils

X. Huang, G. Yang and Z. Chai, Chem. Commun., 2025, 61, 3704 DOI: 10.1039/D4CC06690A

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