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Citation: HE Rong-Xing, LI Ming. Quantum Chemical Study on the Mechanism of Enantioselective Reduction of Aromatic Ketone Catalyzed by Chiral Pyrrolidino [3,4-c] oxazaborolidine[J]. Chinese Journal of Applied Chemistry, ;2002, 19(10): 963-967. shu

Quantum Chemical Study on the Mechanism of Enantioselective Reduction of Aromatic Ketone Catalyzed by Chiral Pyrrolidino [3,4-c] oxazaborolidine

HE Rong-Xing ,
LI Ming ^,

1.
School of Chemistry and Chemical Engineering, Southwest Normal University, Chongqing 400715

Corresponding author: LI Ming,
Received Date: 8 January 2002
Available Online: 25 June 2002
Fund Project:

In quantum chemical studies on enantioselective reductions small model molecules are comonly used to substitute the reactants as reported in literatures. It results in certain neglect of important chemical information. In this paper, the semi-empirical AM1 molecular orbital method is used to study the enantioselective reduction of aromatic ketone catalyzed by chiral pyrrolidino [3,4-c] oxazaborolidine without model substituents. As illustrated, this enantioselective reduction is exothermic. In the transition states of hydrogen atom from the borane moiety to the carbonyl carbon of aromatic ketone, there is a 6-membered B-N-B-H-C-O ring in a twisted chair structure. The controlling step for the reduction is the decomposition of the catalyst:alkoxyborane which contains a B-O-B-N ring.
- chiral pyrrolidino [3,4-c] oxazaborolidine,
- aromatic ketone,
- enantioselective reduction,
- mechanism,
- quantum chemical
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