Marked deuterium isotope effects on the enantioselectivity in rhodium-catalyzed asymmetric hydrogenation of enamides

被引：26
作者：
Imamoto, Tsuneo [2 ]
Itoh, Takuma [2 ]
Yoshida, Kazuhiro [2 ]
Gridnev, Ilya D. [1 ]
机构：
[1] Tokyo Inst Technol, Grad Sch Sci & Engn, Meguro Ku, Tokyo 1528552, Japan
[2] Chiba Univ, Grad Sch Sci, Inage Ku, Yayoi Cho, Chiba 2638522, Japan
来源：
CHEMISTRY-AN ASIAN JOURNAL | 2008年 / 3卷 / 8-9期
关键词：
asymmetric hydrogenation; deuterium; enamides; isotope effects; rhodium;
D O I：
10.1002/asia.200800146
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Deuterium isotope effects on the enantioselectivity in the rhodium-catalyzed asymmetric hydrogenation of enamides and related substrates have been studied. Distinct deuterium isotope effects were observed in the hydrogenation of aryl-substituted enamides having an ortho substituent that is capable of forming a hydrogen bond. The observed isotope effects are interpreted in terms of the competitive reactions of two dihydride intermediates and dideuteride intermediates that exist in equilibrium in the catalytic cycle.
引用
收藏
页码：1636 / 1641
页数：6
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