Access to chiral tertiary amines via the iridium-catalyzed asymmetric hydrogenation of enamines

被引：35

作者：

Cheruku, Pradeep ^{[1
]}

Church, Tamara L. ^{[1
]}

Trifonova, Anna ^{[1
]}

Wartmann, Thomas ^{[1
]}

Andersson, Pher G. ^{[1
]}

机构：

[1] Uppsala Univ, Dept Biochem & Organ Chem, S-75123 Uppsala, Sweden

来源：

TETRAHEDRON LETTERS | 2008年 / 49卷 / 51期

基金：

瑞典研究理事会;

关键词：

Asymmetric catalysis; Hydrogenation; Enamines; Chiral tertiary amines;

D O I：

10.1016/j.tetlet.2008.10.035

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric hydrogenation of N,N-dialkyl and N-alkyl-N-aryl enamines to chiral tertiary amines was studied. All the N,P-ligated iridium complexes investigated were active catalysts for the reaction, but only those with bicycle-supported oxazoline-phosphine ligands gave reasonable stereoinduction. The best catalyst produced a range of chiral tertiary amines in up to 87% ee. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：7290 / 7293

页数：4

共 57 条

[1]

[Anonymous], COMPREHENSIVE ASYMME

[2] A template-based mnemonic for monoamine oxidase (MAO-N) catalyzed reactions and its application to the chemo-enzymatic deracemisation of the alkaloid (±)-crispine A [J].

Bailey, Kevin R. ;

Ellis, Andrew J. ;

Reiss, Renate ;

Snape, Timothy J. ;

Turner, Nicholas J. .

CHEMICAL COMMUNICATIONS, 2007, (35) :3640-3642

[3] Asymmetric hydrogenation of di and trisubstituted enol phosphinates with N,P-ligated iridium complexes [J].

Cheruku, Pradeep ;

Diesen, Jarle ;

Andersson, Pher G. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (16) :5595-5599

[4] Asymmetric hydrogenation of enol phosphinates by iridium catalysts having N,P ligands [J].

Cheruku, Pradeep ;

Gohil, Suresh ;

Andersson, Pher G. .

ORGANIC LETTERS, 2007, 9 (09) :1659-1661

[5] Iridium catalysts for the asymmetric hydrogenation of olefins with nontraditional functional substituents [J].

Church, Tamara L. ;

Andersson, Pher G. .

COORDINATION CHEMISTRY REVIEWS, 2008, 252 (5-7) :513-531

[6] IRIDIUM COMPOUNDS IN CATALYSIS [J].

CRABTREE, R .

ACCOUNTS OF CHEMICAL RESEARCH, 1979, 12 (09) :331-338

[7] Catalytic homogeneous asymmetric hydrogenations of largely unfunctionalized alkenes [J].

Cui, XH ;

Burgess, K .

CHEMICAL REVIEWS, 2005, 105 (09) :3272-3296

[8] Efficient rhodium-catalyzed asymmetric hydrogenation for the synthesis of a new class of N-aryl β-amino acid derivatives [J].

Dai, Q ;

Yang, WR ;

Zhang, XM .

ORGANIC LETTERS, 2005, 7 (23) :5343-5345

[9] Small-molecule H-bond donors in asymmetric catalysis [J].

Doyle, Abigail G. ;

Jacobsen, Eric N. .

CHEMICAL REVIEWS, 2007, 107 (12) :5713-5743

[10] A chemo-enzymatic route to enantiomerically pure cyclic tertiary amines [J].

Dunsmore, CJ ;

Carr, R ;

Fleming, T ;

Turner, NJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (07) :2224-2225

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