Enantioselective hydrogenation of 2-methylquinoxaline to (-)-(2S)-2-methyl-1,2,3,4-tetrahydroquinoxaline by iridium catalysis

被引:128
作者
Bianchini, C
Barbaro, P
Scapacci, G
Farnetti, E
Graziani, M
机构
[1] CNR, Ist Studio Stereochim & Energet Composti Coor, I-50132 Florence, Italy
[2] Univ Trieste, Dipartimento Sci Chim, I-34127 Trieste, Italy
关键词
D O I
10.1021/om980219a
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The orthometalated dihydride complex fac-exo-(R)-[IrH2(C6H4C*H(Me)N(CH2CH2PPh2)(2))] is an effective catalyst precursor for the enantioselective hydrogenation of 2-methylquinoxaline (MeQ) to 2-methyl-1,2,3,4-tetrahydroquinoxaline (MeTHQ) with ee's up to 90% (5 bar of H-2, MeOH, 100 degrees C). In-situ high-pressure NMR spectroscopy in catalytic conditions shows that the catalytically active species is generated by deorthometalation rather than by Ha reductive elimination. H-1 NMR spectroscopy also suggests that the two C=N groups in MeQ are hydrogenated at comparable rates.
引用
收藏
页码:3308 / 3310
页数:3
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