Chiral inducers with (1R,2R)-1,2-diaminocyclohexane core for organo- and metallocatalysis

被引：1

作者：

Gavrilov, Vladislav K. ^{[1
]}

Chuchelkin, Ilya V. ^{[1
]}

Zheglov, Sergey V. ^{[1
]}

Firsin, Ilya D. ^{[1
]}

Shiryaev, Alexei A. ^{[1
]}

Gavrilov, Konstantin N. ^{[1
]}

Maximychev, Alexander V. ^{[2
]}

Perepukhov, Alexander M. ^{[2
]}

Goulioukina, Nataliya S. ^{[3
,4
]}

Beletskaya, Irina P. ^{[3
,4
]}

机构：

[1] SA Esenin Ryazan State Univ, Dept Chem, Ryazan 390000, Russia

[2] Moscow Inst Phys & Technol, Dolgoprudnyi 141700, Moscow Region, Russia

[3] Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119991, Russia

[4] Russian Acad Sci, AN Frumkin Inst Phys Chem & Electrochem, Moscow 119071, Russia

来源：

MENDELEEV COMMUNICATIONS | 2019年 / 29卷 / 01期

基金：

俄罗斯基础研究基金会;

关键词：

PHOSPHITE-PYRIDINE LIGANDS; ALLYLIC SUBSTITUTION; PHOSPHORUS LIGANDS; ASYMMETRIC HYDROGENATION; ALPHA-AMINO; EFFICIENT; CONSTRUCTION; PHOSPHONATES; CATALYSTS;

D O I：

10.1016/j.mencom.2019.01.010

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A P*-chiral diamidophosphite ligand of the 1,3,2-diaza-phospholidine series was obtained by direct phosphorylation of N-(1R,2R)-2-(tert-butoxycarbonylaminocyclohexyl)]-N'-[(1R)-1-(hydroxymethyl)propyl]oxalamide. The use of this ligand made it possible to reach 98% ee in the Pd-catalyzed allylation involving (E)-1,3-diphenylallyl acetate, 81% ee in the allylation of ethyl 2-oxocyclohexane-1-carboxylate with cinnamyl acetate, 78% ee in the Rh-catalyzed hydrogenation of methyl (Z)-2-acetamido-3-phenylacrylate, and 32% ee in the Rh- and Ir-catalyzed hydrosilylation of (E)-N-(4-methoxy-phenyl)-1-phenylethan-1-imine with diphenylsilane. The above mentioned oxalamide provides up to 50% ee in the organocatalytic reduction of the same imine.

引用

页码：35 / 37

页数：3

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