Resolution of Pd catalyst with tropos biphenylphosphine (BIPHEP) ligand by DM-DABN:: Asymmetric catalysis by an enantiopure BIPHEP-Pd complex

被引:77
作者
Mikami, K [1 ]
Aikawa, K [1 ]
Yusa, Y [1 ]
Hatano, M [1 ]
机构
[1] Tokyo Inst Technol, Dept Appl Chem, Tokyo 1528552, Japan
关键词
D O I
10.1021/ol016969p
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
GRAPHICS The racemic Pd complex with the chirally flexible (tropos) biphenylphosphine (BIPHEP) ligand can be resolved with enantiopure 3,3'-dimethyl-2,2'-diamino-1,1'-binaphthyl (DM-DABN) as a resolving agent at room temperature. The enantiopure BIPHEP-Pd complex is obtained from complexation with enantiopure DABN followed by tropo-inversion into the single BIPHEP-Pd diastereomer at 80 degreesC and protonation at 0 degreesC. The enantiopure BIPHEP-Pd complex can be used as an efficient Lewis acid catalyst for the Diels-Alder reaction at room temperature to give high enantioselectivity (82% ee, 60%).
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页码:91 / 94
页数:4
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