Asymmetric Hydrogenation of Seven-Membered C=N-containing Heterocycles and Rationalization of the Enantioselectivity

被引：36

作者：

Balakrishna, Bugga ^{[1
,4
]}

Bauza, Antonio ^{[2
]}

Frontera, Antonio ^{[2
]}

Vidal-Ferran, Anton ^{[1
,3
,4
]}

机构：

[1] Inst Chem Res Catalonia ICIQ, Avinguda Paisos Catalans 16, Tarragona 43007, Spain

[2] Univ Illes Balears, Dept Quim, Km 7-5, Palma De Mallorca 07122, Palma De Mallor, Spain

[3] ICREA, Pg Lluis Companys 23, Barcelona 08010, Spain

[4] Barcelona Inst Sci & Technol, Avinguda Paisos Catalans 16, Tarragona 43007, Spain

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2016年 / 22卷 / 30期

关键词：

asymmetric hydrogenation; enantiopure heterocycles; iridium; phosphine-phosphites; substrate activation; P-OP LIGANDS; CYCLIC IMINES; CATALYTIC PERFORMANCE; BENZODIAZEPINONES;

D O I：

10.1002/chem.201601464

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Iridium(I) complexes with phosphine-phosphite ligands efficiently catalyze the enantioselective hydrogenation of diverse seven-membered C=N-containing heterocyclic compounds (eleven examples; up to 97% ee). The P-OP ligand L3, which incorporates an ortho-diphenyl substituted octahydrobinol phosphite fragment, provided the highest enantioselectivities in the hydrogenation of most of the heterocyclic compounds studied. The observed stereoselection was rationalized by means of DFT calculations.

引用

页码：10607 / 10613

页数：7

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