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Density functional study of organocatalytic mannich‐type reactions: Insight into reverse diastereoselectivities arising from catalysts with different scaffolds
Author(s) -
Tian Changke,
Fu Aiping,
Zhao Chengyan,
Li Hongliang,
Wang Zonghua,
Duan Yunbo
Publication year - 2015
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.24859
Subject(s) - bifunctional , chemistry , catalysis , mannich reaction , density functional theory , selectivity , combinatorial chemistry , computational chemistry , organocatalysis , amino acid , organic chemistry , enantioselective synthesis , biochemistry
Density functional study have been carried out to investigate the stereoselectivities in the Mannich‐type reactions promoted by five typical amino acid catalysts with different scaffolds. The reverse diastereoselectivities in the cyclic and acyclic α‐ and β‐amino acids‐promoted Mannich reactions have been satisfactorily explained by the density functional theory (DFT) methods at the SMD/M06‐2X/6‐31G** computational level. The activation strain analysis has been used to account for the selectivity‐switching for these selected bifunctional catalysts. © 2015 Wiley Periodicals, Inc.