期刊
TETRAHEDRON
卷 71, 期 49, 页码 9339-9345出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2015.10.012
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资金
- Ministerio de Economia y Competitividad of the Spanish Government [CTQ2013-45646-P]
- Ministerio de Economia y Competitividad
- European Social Fund [BES-2014-068258]
The molecular mechanism of the Bronsted acid (BA) catalysed Povarov reaction of N-phenyl-C-methoxycarbonyl imine with a methylenecyclopropane (MCP) has been investigated using DFT methods at the MPWB1K/6-31G(d) level. This BA catalysed Povarov reaction is a domino process initialised by the formation of a cationic intermediate which experiences a quick intramolecular Friedel Crafts reaction yielding the final tetrahydroquinoline. Protonation of the imine nitrogen atom notably increases the electrophilicity of the corresponding species, accelerating the reaction through ionic processes. Analysis of the Parr functions in the initial nucleophilic attack of MCP to the protonated imine allows explaining the total regioselectivity experimentally observed. An electron localisation function quantum topological analysis of the bonding changes along the BA catalysed Povarov reaction permits a complete characterisation of the molecular mechanism. (C) 2015 Elsevier Ltd. All rights reserved.
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