Density functional study of organocatalytic mannich‐type reactions: Insight into reverse diastereoselectivities arising from catalysts with different scaffolds |
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| Authors: | Changke Tian Aiping Fu Chengyan Zhao Hongliang Li Zonghua Wang Yunbo Duan |
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| Affiliation: | Collaborative Innovation Center for Marine Biomass Fibers, Laboratory of New Fiber Materials and Modern Textile, The Growing Base for State Key Laboratory, College of Chemical and Environmental Engineering, Qingdao University, Qingdao, China |
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| Abstract: | 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. |
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| Keywords: | organocatalysis syn‐ and anti‐selective Mannich reactions amino acid DFT |
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