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一种均相催化、两相回收的手性配体的合成及其催化烯烃不对称双羟化反应 被引量：2

The Synthesis of a Chiral Ligand for the Asymmetric Dihydroxylation of Olefins Utilizing One-Phase Catalysis and Two-Phase Recovery
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摘要 A chiral cinchona alkaloid derivative, which can be recovered and reused in asymmetric dihydroxylation (AD) reaction, was easily prepared from 1,4-dichlorophthalazine by two steps. The total yield is 87.4%. Application of this ligand to the AD reaction of six olefins afforded corresponding chiral diols in 92%～98% and 86%～99% ee. After the catalytic reaction, the ligand can be got by filtration from diethyl ether and reused for five runs with good yields and excellent enantioseletivity unchanged. A chiral cinchona alkaloid derivative, which can be recovered and reused in asymmetric dihydroxylation (AD) reaction, was easily prepared from 1,4-dichlorophthalazine by two steps. The total yield is 87.4%. Application of this ligand to the AD reaction of six olefins afforded corresponding chiral diols in 92%～98% and 86%～99% ee. After the catalytic reaction, the ligand can be got by filtration from diethyl ether and reused for five runs with good yields and excellent enantioseletivity unchanged.
作者 王巧峰 孙晓莉 张生勇 秦向阳 金瑛
机构地区 第四军医大学基础部化学教研室
出处 《分子催化》 EI CAS CSCD 北大核心 2004年第2期149-152,共4页 Journal of Molecular Catalysis(China)
基金 国家自然科学基金项目(20272082)资助.
关键词 不对称双羟化反应 可回收手性配体 手性连二醇 Asymmetric dihydroxylation Recoverable chiral ligand Chiral vicinal diols
分类号 O643.32 [理学—物理化学]
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参考文献8

  • 1a Kolb H C, Vannieuwenhze M S, Sharpless K B.Chem Rev[J]. 1994, 94:2483-2 547b Zhang Sheng-yong(张生勇),Guo Jian-quan(郭建权),Asymmetric Catalysis(不对称催化反应)[M].2002, pp. 93-139c Fan Q H, Li Y M, Albert S C Chan.
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同被引文献21

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  • 7Yang X W, Liu H Q, Xu M H. et al. A highly efficient and practical new PEG-bound bi-cinchona alkaloid ligand for the catalytic asymmetric aminohydroxylation of alkenes [ J ]. Tetrahedron :Asym. ,2004,15 ( 12 ) : 1915-1918.
  • 8Kuang Y Q, Zhang S. Y, Jiang R. A free ligand for the asymmetric dihydroxylation of olefins utilizing one-Phase catalysis and two-Phase separation [ J ]. Tetrahedron Lett. , 2002,43:3669-3671.
  • 9Song C E, Jung D. U, Roh E. J, et al. D. Y. Osmium tetroxide - (QN)2PHAL in an ionic liquid: a highly efficient and recyclable catalyst system for asymmetric dihydroxylation of olefins [ J ]. Chem. Commun, 2002,2 ( 24 ) : 3038- 3039.
  • 10Jiang R, Kuang Y. Q, Sun X. L, et al. An improved catalytic system for recycling OsO4 and chiral ligand in asymmetric dihydroxylation of olefins [ J ]. Tetrahedron: Asymmetry,2004,15:743-746.

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分子催化
2004年 第2期

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