Congeners of Troeger's base as chiral ligands |
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Institution: | 1. School of Chemical Engineering, Zhengzhou University, Zhengzhou 450001, China;2. Engineering Research Center of Advanced Manufacturing of Ministry of Education, Zhengzhou University, Zhengzhou 450001, China;3. Department of Chemical Engineering, KU Leuven, Celestijnenlaan 200F, B-3001 Leuven, Belgium;4. Faculty of Engineering and the Built Environment, Tshwane University of Technology, Private Bag X680, Pretoria 0001, South Africa;1. Department of Chemistry, Tsinghua University, Beijing 100084, China;2. Institute of Chemical Materials, CAEP, Mianyang 621900, China |
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Abstract: | (S)-(+)-Troeger's base can be deprotonated and alkylated without loss of stereochemical integrity. An examination of the ability of Troeger's base and several derivatives prepared in this fashion to effect asymmetric induction in the addition of diethylzinc to aromatic aldehydes was conducted. Enantiomeric excesses as high as 86% were achieved, providing evidence that Troeger's base represents a chiral framework which can be modified to produce ligands for catalytic asymmetric synthesis. |
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