CO2-Assisted asymmetric hydrogenation of prochiral allylamines

被引：1

作者：

de Winter, Tamara M. ^{[1
]}

Ho, Jaddie ^{[1
]}

Alridge, Christopher J. ^{[1
]}

Jessop, Philip G. ^{[1
]}

机构：

[1] Queens Univ, Dept Chem, Kingston, ON K7L 3N6, Canada

来源：

RSC ADVANCES | 2022年 / 12卷 / 11期

基金：

加拿大自然科学与工程研究理事会;

关键词：

ENANTIOSELECTIVE HYDROGENATION; CATALYZED HYDROGENATION; DERIVATIVES; OXYTRIFLUOROMETHYLATION; REDUCTION; MECHANISM; CO2;

D O I：

10.1039/d2ra00263a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new methodology for the asymmetric hydrogenation of allylamines takes advantage of a reversible reaction between amines and carbon dioxide (CO2) to suppress unwanted side reactions. The effects of various parameters (pressure, time, solvent, and base additives) on the enantioselectivity and conversion of the reaction were studied. The homogeneously-catalyzed asymmetric hydrogenation of 2-arylprop-2-en-1-amine resulted in complete conversion and up to 82% enantiomeric excess (ee). Added base, if chosen carefully, improves the enantioselectivity and chemoselectivity of the overall reaction.

引用

页码：6755 / 6761

页数：7

共 34 条

[1] Stereoselective Rh-catalyzed hydrogenation of cyclobutyl chiral enamides:: Double stereodifferentiation vs catalyst-controlled diastereoselection [J].

Aguado, GP ;

Moglioni, AG ;

García-Expósito, E ;

Branchadell, V ;

Ortuño, RM .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (23) :7971-7978

[2] Highly enantioselective hydrogenation of itaconic acid derivatives with a chiral bisphospholane-Rh(I) catalyst [J].

Almena, J ;

Monsees, A ;

Kadyrova, R ;

Riermeier, TH ;

Gotov, B ;

Holz, J ;

Börner, A .

ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (11) :1263-1266

[3] Iridium-Catalyzed Asymmetric Hydrogenation of Unfunctionalized Enamines [J].

Baeza, Alejandro ;

Pfaltz, Andreas .

CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (10) :2266-2269

[4] SYNTHESIS OF AN OPTICALLY-ACTIVE PHENIRAMINE BY ENANTIOSELECTIVE HYDROGENATION CATALYZED BY BINAP RUTHENIUM(II) COMPLEXES [J].

BOTTEGHI, C ;

DELPONTE, G ;

MARCHETTI, C .

JOURNAL OF MOLECULAR CATALYSIS, 1993, 83 (1-2) :L1-L4

[5] A convenient asymmetric synthesis of alpha-1-arylalkylamines through the enantioselective hydrogenation of enamides [J].

Burk, MJ ;

Wang, YM ;

Lee, JR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (21) :5142-5143

[6] Hydrogenation of nitrile in supercritical carbon dioxide: a tunable approach to amine selectivity [J].

Chatterjee, Maya ;

Kawanami, Hajime ;

Sato, Masahiro ;

Ishizaka, Takayuki ;

Yokoyama, Toshirou ;

Suzuki, Toshishige .

GREEN CHEMISTRY, 2010, 12 (01) :87-93

[7] Enantioselective Synthesis of α-Trifluoromethyl Arylmethylamines by Ruthenium-Catalyzed Transfer Hydrogenation Reaction [J].

Dai, Xiaoyang ;

Cahard, Dominique .

ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (06) :1317-1328

[8] Synthesis of optically active 2-aminotetraline derivatives via enantioselective ruthenium-catalyzed hydrogenation of ene carbamates [J].

Dupau, P ;

Hay, AE ;

Bruneau, C ;

Dixneuf, PH .

TETRAHEDRON-ASYMMETRY, 2001, 12 (06) :863-867

[9] Enantioselective rhodium-catalyzed hydrogenation of enol carbamates in the presence of monodentate phosphines [J].

Enthaler, Stephan ;

Erre, Giulia ;

Junge, Kathrin ;

Michalik, Dirk ;

Spannenberg, Anke ;

Marras, Fabrizio ;

Gladiali, Serafino ;

Beller, Matthias .

TETRAHEDRON-ASYMMETRY, 2007, 18 (11) :1288-1298

[10] HOMOGENEOUS HYDROGENATION AND HYDROFORMYLATION USING RUTHENIUM COMPLEXES [J].

EVANS, D ;

OSBORN, JA ;

JARDINE, FH ;

WILKINSON, G .

NATURE, 1965, 208 (5016) :1203-+

← 1 2 3 4 →