Lewis acid catalyzed diastereoselective [3+4]-annulation of donor-acceptor cyclopropanes with anthranils: synthesis of tetrahydro-1-benzazepine derivatives

Zhe-Hao Wang; Huan-Huan Zhang; Dao-Ming Wang; Peng-Fei Xu; Yong-Chun Luo

doi:10.1039/c7cc04239f

Lewis acid catalyzed diastereoselective [3+4]-annulation of donor-acceptor cyclopropanes with anthranils: synthesis of tetrahydro-1-benzazepine derivatives

Chem Commun (Camb). 2017 Jul 27;53(61):8521-8524. doi: 10.1039/c7cc04239f.

Authors

Zhe-Hao Wang¹, Huan-Huan Zhang¹, Dao-Ming Wang¹, Peng-Fei Xu¹, Yong-Chun Luo¹

Affiliation

¹ State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China. luoych@lzu.edu.cn.

PMID: 28707695
DOI: 10.1039/c7cc04239f

Abstract

A Lewis acid catalyzed [3+4]-annulation reaction between cyclopropane 1,1-diesters and anthranils has been developed. This annulation consists of a reaction sequence involving ring-opening/aromatization/nucleophilic addition. Thereinto, aromatization is the driving force for this annulation. Using this reaction, a series of 8-oxa-1-azabicyclo[3.2.1]octanes can be prepared conveniently with excellent diastereoselectivity.