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

Chem Commun (Camb)

State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China.

Published: July 2017

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.

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http://dx.doi.org/10.1039/c7cc04239fDOI Listing

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