| 噁唑硼烷对苯甲酮不对称还原反应催化性能的理论计算 |
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| 引用本文： | 樊建芬,黄洁,卢运祥,孙云鹏.噁唑硼烷对苯甲酮不对称还原反应催化性能的理论计算[J].化学研究,2005,16(3):58-61. |
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| 作者姓名： | 樊建芬 黄洁 卢运祥 孙云鹏 |
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| 作者单位： | 苏州大学,化学系,江苏,苏州,215006;苏州大学,化学系,江苏,苏州,215006;苏州大学,化学系,江苏,苏州,215006;苏州大学,化学系,江苏,苏州,215006 |
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| 摘 要： | 采用AM1方法研究了四种1,3,2-噁唑硼烷催化剂对苯甲酮不对称还原反应的催化性能,计算了立体控制步骤中生成R和S型催化配合物的反应热和活化能,并根据立体控制步骤中R和S型过渡态的熵和焓等参数,计算了四种催化反应体系最终产物的绝对构型及光学活性(e.e.%),据此对四种催化剂的对映选择性作出了评价.
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| 关 键 词： | AM1 苯甲酮 不对称还原反应 对映选择性 噁唑硼烷催化剂 |
| 文章编号： | 1008-1011（2005）03-0058-04 |
| 收稿时间： | 2005-03-24 |
| 修稿时间： | 2005年3月24日 |
Theoretical Study on Enantioselectivity of Oxazaborolidine Catalysts for Reduction of Phenyl Methyl Ketone |
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| FAN Jian-fen,HUANG Jie,LU Yun-xiang,SUN Yun-peng.Theoretical Study on Enantioselectivity of Oxazaborolidine Catalysts for Reduction of Phenyl Methyl Ketone[J].Chemical Research,2005,16(3):58-61. |
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| Authors: | FAN Jian-fen HUANG Jie LU Yun-xiang SUN Yun-peng |
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| Abstract: | The AM1-SCF MO method has been applied to study the enantioselectivities of four kinds of 1,3,2-oxazaborolidine as the catalysts in the reduction of phenyl methyl ketone.The optimized geometries,thermal anthalpies and entropies of R and S transition states in the stereo-controlling steps of the four catalyzed-reductions have been obtained.The absolute configurations and optical activities(e.e.% values) of the final products are calculated.It was found that(S)-3-methyl-4-benzyl-5,5-diphenyl-1,3,2-oxazaborolidine shows better enantioselectity in the catalysts. |
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| Keywords: | AM1 phenyl methyl ketone enantioselective reduction enantioselectivity oxazaborolidine catalyst |
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