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The mechanism investigation of the imidazolidinone catalyzed five‐membered ring synthesis reaction
Author(s) -
Zhang Lili,
Liu Huiling,
Yang Yuhong,
Chong Zhihui,
Feng Tingting,
Huang Xuri
Publication year - 2013
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.3073
Subject(s) - chemistry , michael reaction , intramolecular force , tautomer , enamine , enol , catalysis , reaction mechanism , computational chemistry , mechanism (biology) , density functional theory , ring (chemistry) , hydrolysis , organic chemistry , combinatorial chemistry , philosophy , epistemology
The intramolecular asymmetric Michael addition reaction catalyzed by imidazolidinone is investigated using the density functional theory calculations. The details of the reaction mechanism, potential energy surfaces, and the influence of the acid additive are investigated. The reaction process includes two stages. The first stage is Michael addition , in which the enamine complex is created and then the Michael addition is carried out. The second stage is a product separation stage which includes an enol‐keto tautomerization and a two‐step hydrolysis . The enantioselectivity is controlled by the Michael addition step which involves a new carbon–carbon bond formation . The calculation results provide a general model which may explain the mechanism and enantioselectivity of the title reaction. Copyright © 2012 John Wiley & Sons, Ltd.