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

共 50 条

[31] Comment on "Comment on "Crystallographic and theoretical study of the atypical distorted octahedral geometry of the metal chromophore of zinc(II) bis((1R,2R)-1,2-diaminocyclohexane) dinitrate""
Ivanova, Bojidarka
JOURNAL OF MOLECULAR STRUCTURE, 2023, 1287
[32] New chiral macrocyclic lanthanide complexes derived from (IR,2R)-1,2-diaminocyclohexane and 2,6-diformylpyridine
Lisowski, J
Gregolinski, J
Switalska, M
Wiglusz, K
INORGANICA CHIMICA ACTA, 2005, 358 (11) : 3015 - 3023
[33] Solubility and Thermodynamic Properties of (1R,2R)-(+)-1,2-Diaminocyclohexane L-Tartrate in Methanol (Ethanol or 2-Propanol) + Water Binary Solvents at Various Temperatures
Haihan Huanxin Li
Yonghui Zhang
Li Dou
Guoji Xu
Russian Journal of Physical Chemistry A, 2019, 93 : 696 - 702
[34] [N,N′-bis-(6-methylpyrid-2-ylium)-(1R,2R)-1,2-diaminocyclohexane] bis-[(p-cymene)-trichlorouthenate(II)]
Cabeza, JA
da Silva, I
del Río, I
García-Granda, S
APPLIED ORGANOMETALLIC CHEMISTRY, 2005, 19 (01) : 209 - 210
[35] (1R,2R)-1,2-DIPHENYL-1,2-ETHANEDIAMINE MONOHYDROBROMIDE
FERGUSON, G
GALLAGHER, JF
FULLWOOD, R
PARKER, D
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1992, 48 : 2273 - 2275
[36] trans-(1R,2R)-diaminocyclohexane-functionalized mesoporous organosilica spheres as chiral stationary phase
Zhu, Guiru
Jiang, Dongmei
Yang, Qihua
Yang, Jie
Li, Can
JOURNAL OF CHROMATOGRAPHY A, 2007, 1149 (02) : 219 - 227
[37] Mesoporous ethane-silicas functionalized with trans-(1R,2R)-diaminocyclohexane as heterogeneous chiral catalysts
Jiang, DM
Yang, QH
Yang, J
Zhang, L
Zhu, GR
Su, WG
Li, C
CHEMISTRY OF MATERIALS, 2005, 17 (24) : 6154 - 6160
[38] Novel NMR chiral solvating agents derived from (1R,2R)-diaminocyclohexane:: synthesis and enantiodiscrimination for chiral carboxylic acids
Yang, Xuemei
Wang, Guitao
Zhong, Cheng
Wu, Xiaojun
Fu, Enqin
TETRAHEDRON-ASYMMETRY, 2006, 17 (06) : 916 - 921
[39] Solubility and Thermodynamic Properties of (1R,2R)-(+)-1,2-Diaminocyclohexane L-Tartrate in Methanol (Ethanol or 2-Propanol) plus Water Binary Solvents at Various Temperatures
Li, Huanxin
Zhang, Haihan
Dou, Yonghui
Xu, Li
Liu, Guoji
RUSSIAN JOURNAL OF PHYSICAL CHEMISTRY A, 2019, 93 (04) : 696 - 702
[40] Monoimines derived from (1R, 2R)-1,2-diaminocyclohexane in aza-Diels-Alder reaction: Synthesis and characterization of sulfur derivatives based on the 2-azanorbornyl skeleton
Dorsz, Mateusz
Kleniewska, Karolina
Wojaczynska, Elzbieta
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2016, 191 (02) : 279 - 282

← 1 2 3 4 5 →