Special Issue "Organocatalysis"

Guest Editor
Dr. Guofu Zhong
Division of Chemistry and Biological Chemistry, Nanyang Technological University, 21 Nanyang Link, Singapore 637371, Singapore
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• small molecule catalyst
• organic catalyst
• organocatalyst
• enamine catalysis
• iminium catalysis
• N-heterocyclic carbenes
• phase transfer catalysis
• H-bond catalysis
• organocatalysis
• small molecule catalyzed reactions
• organocatalytic reactions
• organocatalytic tandem reactions
• organocatalytic domino reactions
• organocatalytic cascade reactions
• organocatalytic asymmetric reactions

Title: Catalytic Stereoselective Reduction of Ketoimines with Trichlorosilane Promoted by Novel Chiral Lewis Bases §
Authors: Stefania Guizzetti and Maurizio Benaglia
Affiliation: Dipartimento di Chimica Organica e Industriale, Universita' di Milano, via C. Golgi 19, I-20133 Milano, Italy
Abstract: The straightforward synthesis of a series of enantiomerically pure Lewis basic amides by simple condensation of commercially available enantiopure amino alcohol with oxalic acid derivatives is reported. These compounds were shown to promote the enantioselective reduction of ketoimines with trichlorosilane. Working with the model substrate N-phenyl benzophenone imine the new organocatalysts lead to the formation of the corresponding amine with excellent chemical efficiency (up to 99% chemical yield) and good stereoselectivity (up to 63% ee).

Type of Paper: Article
Title: Contribution of Cation-pi Interaction in Iminium Catalysis
Author: Shinji Yamada
Affiliation: Department of Chemistry Ochanomizu University, Japan; E-Mail: yamada.shinji@ocha.ac.jp
Abstract: MacMillan and co-workers have developed a series of chiral imidazolidinones as powerful enantioselective catalysts forc arbon-carbon bond-forming reactions. The high enantio selectivities canbe explained by the preference in the closed conformation of the iminium intermediate, which was explored by calculations. We clarified that an iminium-pi interaction is the origin of the preference in the closed conformation by comparison with the optimized structures for the corresponding non-charged C-analogues.