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苯乙胺衍生的手性膦-亚磷酰胺酯配体在Rh-催化α-烯醇酯膦酸酯的不对称氢化反应中的应用

Rh-Catalyzed Asymmetric Hydrogenation of α-Enol Ester Phosphonates with 1-Phenylethylamine-Derived Phosphine-Phosphoramidite Ligands

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【作者】 胡娟王道永郑卓胡向平

【Author】 HU Juan,WANG Dao-yong,ZHENG Zhuo*,HU Xiang-ping*(Dalian Institute of Chemical Physics,Chinese Academy of Sciences,Dalian 116023,China)

【机构】 中国科学院大连化学物理研究所

【摘要】 将苯乙胺衍生的手性膦-亚磷酰胺酯配体应用在Rh-催化α-烯醇酯膦酸酯的不对称氢化反应中,考察了配体结构及反应条件对反应结果的影响,并在优化的条件下研究了各种底物的适用范围,产物的对映选择性最高>99%ee.

【Abstract】 A series of phosphine-phosphoramidite ligands derived from commercially available,inexpensive chiral 1-phenylethylamine were employed in the Rh-catalyzed asymmetric hydrogenation of various α-enol ester phosphonates.The results indicated that the ligand(Sc,Sa)-2b bearing a Me-group on amino moiety exhibited similar enantioselectivity but superior catalytic activity to(Rc,Ra)-THNAPhos.Excellent enantioselectivities(up to >99% ee) and high catalytic activity(S/C up to 5 000) have been achieved in the hydrogenation of various β-alkyl and β-aryl substituted substrates,demonstrating the high potential of this phosphine-phosphoramidite ligand in the preparation of optically active α-hydroxyphosphonates

【基金】 国家自然科学基金(No.20972156)
  • 【文献出处】 分子催化 ,Journal of Molecular Catalysis , 编辑部邮箱 ,2012年06期
  • 【分类号】O643.32
  • 【被引频次】6
  • 【下载频次】138
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