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

被引：129

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

来源：

ORGANOMETALLICS | 1998年 / 17卷 / 15期

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.

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页码：3308 / 3310

页数：3

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