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Quantum chemical study on asymmetric catalysis reduction of imine

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Abstract

The quantum chemical method is employed to study the enantioselective reduction of imine with borane catalyzed by chiral oxazaborolidine. All the structures are optimized completely at the B3LYP/6-31G(d) level. The catalysis property of oxazaborolidine is notable. The reduction goes mainly through the formations of the catalyst-borane adduct, the catalyst-borane-imine adduct, and the catalyst-amidoborane adduct and the dissociation of the catalyst-amidoborane adduct with the regeneration of the catalyst. The controlling step for the reduction is the dissociation of the catalyst-amidoborane adduct. The main reduced product predicted theoretically is (R)-secondary amine, which is in agreement with the experiment.

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Authors and Affiliations

  1. Department of Chemistry, Southwest-China Normal University, 400715, Chongqing, China

    Li Ming

  2. Department of Chemistry, Sichuan University, 610064, Chengdu, China

    Tian Anmin

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  1. Li Ming
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  2. Tian Anmin
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Correspondence to Li Ming.

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Ming, L., Anmin, T. Quantum chemical study on asymmetric catalysis reduction of imine. Sc. China Ser. B-Chem. 46, 124–131 (2003). https://doi.org/10.1360/03yb9018

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