Iridium/f-Amphol-catalyzed Efficient Asymmetric Hydrogenation of Benzo-fused Cyclic Ketones

被引：32

作者：

Yin, Congcong ^{[1
]}

Dong, Xiu-Qin ^{[1
]}

Zhang, Xumu ^{[1
,2
,3
]}

机构：

[1] Wuhan Univ, Coll Chem & Mol Sci, Minist Educ, Key Lab Biomed Polymers,Engn Res Ctr Organosilico, Wuhan 430072, Hubei, Peoples R China

[2] Southern Univ Sci & Technol, Dept Chem, Shenzhen 518055, Guangdong, Peoples R China

[3] Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Shenzhen 518055, Guangdong, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2018年 / 360卷 / 22期

基金：

中国国家自然科学基金;

关键词：

Asymmetric hydrogenation; Benzo-fused cyclic ketone; Chiral benzo-fused cyclic alcohol; Enantioselectivity; Phosphorus ligand; DYNAMIC KINETIC RESOLUTION; ENANTIOSELECTIVE HYDROGENATION; RUTHENIUM CATALYSTS; ARYL KETONES; PROCHIRAL KETONES; AROMATIC KETONES; LIGANDS; COMPLEXES; HYDROSILYLATION; REDUCTION;

D O I：

10.1002/adsc.201800839

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Iridium/f-Amphol-catalyzed asymmetric hydrogenation of various benzo-fused five to seven-membered cyclic ketones was successfully developed, affording a series of chiral benzo-fused cyclic alcohols with excellent results (75%-99% yields, 93%->99% ee, and TON up to 297 000). The enantioenriched products can be employed as key intermediates or motifs for the synthesis of some important biologically active compounds, such as rasagiline mesylate TVP-1012 used for the treatment of Parkinson's disease, the enantiomer of anticonvulsant drug eslicarbazepine acetate (BIA 2-093).

引用

页码：4319 / 4324

页数：6

共 44 条

[1]

[Anonymous], 2017, Angew. Chem

[2] A series of novel β-hydroxyamide based catalysts for borane-mediated enantioselective reductions of prochiral ketones [J].

Azizoglu, Murat ;

Erdogan, Asli ;

Arslan, Nevin ;

Turgut, Yilmaz ;

Hosgoren, Halil ;

Pirinccioglu, Necmettin .

TETRAHEDRON-ASYMMETRY, 2016, 27 (14-15) :614-622

[3] β-Hydroxyamide-Based Ligands and Their Use in the Enantioselective Borane Reduction of Prochiral Ketones [J].

Azizoglu, Murat ;

Erdogan, Asli ;

Arslan, Nevin ;

Turgut, Yilmaz .

CHIRALITY, 2014, 26 (01) :21-26

[4] Hydrogen: a good partner for rhodium-catalyzed hydrosilylation [J].

Balan, Cedric ;

Pop, Roxana ;

Comte, Virginie ;

Poinsot, Didier ;

Ratovelomanana-Vidal, Virginie ;

Le Gendre, Pierre .

APPLIED ORGANOMETALLIC CHEMISTRY, 2014, 28 (07) :517-522

[5]

Begue J. P., 1992, J CHEM SOC P1, V22, P3141

[6] Iminophenyl Oxazolinylphenylamine for Enantioselective Cobalt-Catalyzed Hydrosilylation of Aryl Ketones [J].

Chen, Xu ;

Lu, Zhan .

ORGANIC LETTERS, 2016, 18 (18) :4658-4661

[7] SYNTHESIS AND DOPAMINE AGONIST PROPERTIES OF (+/-)-TRANS-3,4,4A,10B-TETRAHYDRO-4-PROPYL-2H,5H-[1]BENZOPYRANO[4,3-B]-1,4-OXAZIN-9-OL AND ITS ENANTIOMERS [J].

DEWALD, HA ;

HEFFNER, TG ;

JAEN, JC ;

LUSTGARTEN, DM ;

MCPHAIL, AT ;

MELTZER, LT ;

PUGSLEY, TA ;

WISE, LD .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (01) :445-450

[8] Recent Developments in Asymmetric Hydrogenation and Transfer Hydrogenation of Ketones and Imines through Dynamic Kinetic Resolution [J].

Echeverria, Pierre-Georges ;

Ayad, Tahar ;

Phansavath, Phannarath ;

Ratovelomanana-Vidal, Virginie .

SYNTHESIS-STUTTGART, 2016, 48 (16) :2523-2539

[9] Application of chiral mixed phosphorus/sulfur ligands to enantioselective rhodium-catalyzed dehydroamino acid hydrogenation and ketone hydrosilylation processes [J].

Evans, DA ;

Michael, FE ;

Tedrow, JS ;

Campos, KR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (12) :3534-3543

[10] Enantioselective synthesis of cis-α-substituted cycloalkanols and trans-cycloalkyl amines thereof [J].

Fernandez, Rosario ;

Ros, Abel ;

Magriz, Antonio ;

Dietrich, Hansjoerg ;

Lassaletta, Jose M. .

TETRAHEDRON, 2007, 63 (29) :6755-6763

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