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On the formation of a side product with hexahydroaporphine-like structure in the Grewe cyclization of dextromethorphan

Journal article
Authors Qiao Zhao
Kai Zhao
Sheng ying Wu
Bo xue Tian
Leif A Eriksson
Li min Wang
Na An
Zhong zhu Long
Shui hong Cai
Published in Research on Chemical Intermediates
Volume 43
Issue 3
Pages 1689–1708
ISSN 0922-6168
Publication year 2017
Published at Department of Chemistry and Molecular Biology
Pages 1689–1708
Language en
Links doi.org/10.1007/s11164-016-2723-4
Keywords Dextromethorphan, DFT calculation, Grewe cyclization, Hexahydroaporphine-like side product
Subject categories Quantum chemistry, Organic synthesis

Abstract

Factors leading to the formation of a hexahydroaporphine-like cyclizing side product were studied systematically for the first time and the ratio of this side product was controlled effectively. To understand better the electronic effect of substrates on the formation of side products, different 1-benzyloctahydroisoquinolines with substituted groups on nitrogen or benzene ring were compared. A plausible mechanism of cyclizing reaction was proposed, and key intermediates as well as transition states were analyzed using DFT calculations.

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