Ruthenium-Catalyzed Enantioselective Hydrogenation of Ferrocenyl Ketones: A Synthetic Method for Chiral Ferrocenyl Alcohols

被引：9

作者：

Lu, Bin ^{[1
]}

Wang, Qun ^{[1
]}

Zhao, Mengmeng ^{[1
]}

Xie, Xiaomin ^{[1
]}

Zhang, Zhaoguo ^{[1
,2
]}

机构：

[1] Shanghai Jiao Tong Univ, Sch Chem & Chem Engn, Shanghai 200240, Peoples R China

[2] Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 19期

基金：

中国国家自然科学基金;

关键词：

ASYMMETRIC TRANSFER HYDROGENATION; BETA-HYDROXY ESTERS; DIPHOSPHINE LIGANDS; HIGHLY EFFICIENT; ALLYLIC ALKYLATION; COMPLEXES; HYDROBORATION; SUBSTITUENTS; DIETHYLZINC; MECHANISM;

D O I：

10.1021/acs.joc.5b01548

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Highly effective asymmetric hydrogenation of various ferrocenyl ketones, including aliphatic ferrocenyl ketones as well as the more challenging aryl ferrocenyl ketones, was realized in the presence of a Ru/diphosphine/diamine bifunctional catalytic system. Excellent enantioselectivities (up to 99.8% cc) and activities (S/C = 5000) could be obtained. These asymmetric hydrogenations provided a convenient and efficient synthetic method for chiral ferrocenyl alcohols, which are key intermediates for a variety of chiral ferrocenyl ligands and resolving reagents.

引用

页码：9563 / 9569

页数：7

共 85 条

[1] Mechanism of the hydrogenation of ketones catalyzed by trans-dihydrido(diamine)ruthenium(II) complexes [J].

Abdur-Rashid, K ;

Clapham, SE ;

Hadzovic, A ;

Harvey, JN ;

Lough, AJ ;

Morris, RH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (50) :15104-15118

[2] Catalytic cycle for the asymmetric hydrogenation of prochiral ketones to chiral alcohols:: Direct hydride and proton transfer from chiral catalysts trans-Ru(H)2(diphosphine)(diamine) to ketones and direct addition of dihydrogen to the resulting hydridoamido complexes [J].

Abdur-Rashid, K ;

Faatz, M ;

Lough, AJ ;

Morris, RH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (30) :7473-7474

[3]

Anguille S., 2001, J CHEM SOC P2, V4, P639

[4]

[Anonymous], 2007, The Handbook of Homogeneous Hydrogenation

[5] A NEW CHIRAL TRIDENTATE FERROCENYL LIGAND - SYNTHESIS AND CHARACTERIZATION OF ITS PALLADIUM(II) AND NICKEL(II) COMPLEXES [J].

BARBARO, P ;

TOGNI, A .

ORGANOMETALLICS, 1995, 14 (07) :3570-3573

[6] Acylations with Long-Chain Acid Anhydrides and Acyl Chlorides over Zeolite Beta [J].

Bejblova, M. ;

Prochazkova, D. ;

Vlk, J. .

TOPICS IN CATALYSIS, 2009, 52 (1-2) :178-184

[7] Phosphinoferrocenylaminophosphines as novel and practical ligands for asymmetric catalysis [J].

Boaz, NW ;

Debenham, SD ;

Mackenzie, EB ;

Large, SE .

ORGANIC LETTERS, 2002, 4 (14) :2421-2424

[8] Catalytic enantioselective aryl transfer:: asymmetric addition of diphenylzinc to aldehydes [J].

Bolm, C ;

Muñiz, K .

CHEMICAL COMMUNICATIONS, 1999, (14) :1295-1296

[9] Catalyzed asymmetric aryl transfer reactions to aldehydes with boronic acids as aryl source [J].

Bolm, C ;

Rudolph, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (50) :14850-14851

[10] Catalytic enantioselective addition of diethylzinc to aldehydes using aziridine based chiral ligands [J].

Bulut, Adnan ;

Aslan, Ayhan ;

Izgu, Enver Cagri ;

Dogan, Oezdemir .

TETRAHEDRON-ASYMMETRY, 2007, 18 (08) :1013-1016

← 1 2 3 4 5 6 7 8 9 →