Theoretical Investigation on the Role of Amine Bases in Stabilizing the Key Intermediate of Proline Enamine Carboxylate in Proline-Catalyzed Asymmetric Reactions

Chang Ke Tian; Ai Ping Fu; Cheng Yan Zhao; Feng Hui Tian; Yun Bo Duan; Zong Hua Wang

doi:10.4028/www.scientific.net/AMR.998-999.124

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HomeAdvanced Materials ResearchAdvanced Materials Research Vols. 998-999Theoretical Investigation on the Role of Amine...

Theoretical Investigation on the Role of Amine Bases in Stabilizing the Key Intermediate of Proline Enamine Carboxylate in Proline-Catalyzed Asymmetric Reactions

Abstract:

Quantum mechanical calculations have been performed to study the equilibrium among the key intermediates (iminium ion, oxazolidione, and enamine) in the proline-catalyzed reactions under base-free and base-present conditions. The results confirmed that the tautomeric equilibrium among these species can be tuned by the basic additives. The computations satisfactorily rationalized the experimental observations and provide a clue on how to stabilize the enamine intermediates.

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Periodical:

Advanced Materials Research (Volumes 998-999)

Pages:

124-127

DOI:

https://doi.org/10.4028/www.scientific.net/AMR.998-999.124

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Online since:

July 2014

Authors:

Chang Ke Tian, Ai Ping Fu*, Cheng Yan Zhao, Feng Hui Tian, Yun Bo Duan, Zong Hua Wang

Keywords:

Amine Bases, DFT, Enamine Carboxylate, Organocatalysis

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