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The study on reaction mechanism and diastereoselectivitiy of hydride reduction
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- Kaneno Daisuke
- Graduate School of Integrated Arts and Sciences, Kochi University
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- Suzuki Yasumitsu
- Graduate School of Engineering, The University of Tokyo
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- Tomoda Shuji
- Graduate School of Arts and Sciences, The University of Tokyo
Bibliographic Information
- Other Title
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- 面選択ヒドリド還元の反応機構解析
Description
As the first step to understand the reaction mechanism and diastereoselectivity of sodium borohydride reduction of ketones, ab initio Car-Parrinello molecular dynamics simulation has been performed on a solution of NaBH4 in methanol. According to pointwise thermodynamic integration involving constrained molecular dynamics simulations, it was strongly suggested that Na+ and BH4- are associated in the solvent forming contact ion pairs. Thus we propose a new transition state structure model that contains complexation of the carbonyl oxygen with sodium cation. Predicted diastereoselectivity of the reduction of some substituted cyclohexanones applying this novel transition state model is in good agreement with experimental data, showing its validity and effectiveness to investigate the diastereoselectivity of NaBH4 reduction of other ketones.
Journal
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- Abstracts of Symposium on Physical Organic Chemistry
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Abstracts of Symposium on Physical Organic Chemistry 2009 (0), 16-16, 2009
The Society of Physical Organic Chemistry, Japan
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Keywords
Details 詳細情報について
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- CRID
- 1390282680533320960
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- NII Article ID
- 130004728768
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- Text Lang
- ja
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- Data Source
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- JaLC
- CiNii Articles
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- Abstract License Flag
- Disallowed
