Enantioselective Reaction Using Palladium Pincer Complexes with C2-Symmetric Chiral Bis(imidazoline)s

被引:0
作者
Nakamura, Shuichi [1 ]
机构
[1] Nagoya Inst Technol, Grad Sch Engn, Dept Frontier Mat, Showa Ku, Nagoya, Aichi 4668555, Japan
关键词
FRIEDEL-CRAFTS ALKYLATION; OPTICALLY-ACTIVE PROPARGYLAMINES; BAYLIS-HILLMAN REACTION; ASYMMETRIC-SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; DECARBOXYLATIVE ADDITION; QUATERNARY STEREOCENTERS; 3-COMPONENT SYNTHESIS; MARINE ALKALOIDS; BENZYL NITRILES;
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The development of novel chiral catalysts is one of the most challenging areas in organic chemistry. This account summarizes our recent studies on chiral bis(imidazoline)-palladium pincer type catalysts (phebim-Pd). The catalysts can be used in the enantioselective reaction of a wide variety of nitrile compounds with imines giving products in high yields with good stereoselectivities. This process offers a simple and efficient route for the synthesis of functionalized beta-aminonitriles and their derivatives. We also examine the enantioselective allylation of ketimines derived from isatins using chiral phebim-Pd complexes to afford products in high yields with good enantioselectivities.
引用
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页码:8 / 17
页数:10
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[91]   Catalytic enantioselective allylation of ketoimines [J].
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[93]   Recent Advances in Catalytic Asymmetric Decarboxylative Addition Reactions [J].
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Hao, Xin-Qi ;
Xu, Yan-Xiao ;
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Wang, Ya-Nan ;
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Song, Mao-Ping .
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Gong, Jun-Fang ;
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[96]   Direct Catalytic Asymmetric Addition of Allylic Cyanides to Ketoimines [J].
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