Gold(I)-Catalyzed Amination of Allylic Alcohols with Cyclic Ureas and Related Nucleophiles

被引：86

作者：

Mukherjee, Paramita ^{[1
]}

Widenhoefer, Ross A. ^{[1
]}

机构：

[1] Duke Univ, Dept Chem, French Family Sci Ctr, Durham, NC 27708 USA

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 06期

关键词：

CATALYZED DIRECT AMINATION; PALLADIUM; ALLYLATION; COMPLEXES; EFFICIENT; AMINES; ALKYLATION; SECONDARY; LIGANDS; SULFONAMIDES;

D O I：

10.1021/ol902923e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A 1:1 mixture of [P(t-Bu)(2)-o-biphenyl]AuCl and AgSbF6 catalyzes the Intermolecular amination of allylic alcohols with 1-methylimidazolidin-2-one and related nucleophiles that, in the case of gamma-unsubstituted or gamma-methyl-substituted allylic alcohols, occurs with high gamma-regloselectivity and syn-stereoselectivity.

引用

页码：1184 / 1187

页数：4

共 49 条

[1] Au-catalyzed cyclization of monoallylic diols [J].

Aponick, Aaron ;

Li, Chuan-Ying ;

Biannic, Berenger .

ORGANIC LETTERS, 2008, 10 (04) :669-671

[2] An Extremely Facile Synthesis of Furans, Pyrroles, and Thiophenes by the Dehydrative Cyclization of Propargyl Alcohols [J].

Aponick, Aaron ;

Li, Chuan-Ying ;

Malinge, Jeremy ;

Marques, Emerson Finco .

ORGANIC LETTERS, 2009, 11 (20) :4624-4627

[3] Au-Catalyzed Cyclization of Monopropargylic Triols: An Expedient Synthesis of Monounsaturated Spiroketals [J].

Aponick, Aaron ;

Li, Chuan-Ying ;

Palmes, Jean A. .

ORGANIC LETTERS, 2009, 11 (01) :121-124

[4] Enantioselective Gold-Catalyzed Allylic Alkylation of Indoles with Alcohols: An Efficient Route to Functionalized Tetrahydrocarbazoles [J].

Bandini, Marco ;

Eichholzer, Astrid .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (50) :9533-9537

[5] Syntheses and X-ray crystal structures of cationic, two-coordinate gold(I) π-alkene complexes that contain a sterically hindered o-biphenylphosphine ligand [J].

Brown, Timothy J. ;

Dickens, Marina G. ;

Widenhoefer, Ross A. .

CHEMICAL COMMUNICATIONS, 2009, (42) :6451-6453

[6] Syntheses, X-ray Crystal Structures, and Solution Behavior of Monomeric, Cationic, Two-Coordinate Gold(I) π-Alkene Complexes [J].

Brown, Timothy J. ;

Dickens, Marina G. ;

Widenhoefer, Ross A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (18) :6350-+

[7] Cationic NHC-gold(I) complexes: Synthesis, isolation, and catalytic activity [J].

de Fremont, Pierre ;

Marion, Nicolas ;

Nolan, Steven P. .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2009, 694 (04) :551-560

[8] Iridium-catalyzed synthesis of primary allylic amines from allylic alcohols: Sulfamic acid as amonia equivalent [J].

Defieber, Christian ;

Ariger, Martin A. ;

Moriel, Patricia ;

Carreira, Erick M. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (17) :3139-3143

[9] Gold (III)-catalyzed direct nucleophilic substitution of propargylic alcohols [J].

Georgy, Marie ;

Boucard, Valerie ;

Debleds, Olivier ;

Dal Zotto, Christophe ;

Campagne, Jean-Marc .

TETRAHEDRON, 2009, 65 (09) :1758-1766

[10] Gold-catalyzed direct amination of allylic alcohols [J].

Guo, Shenghai ;

Song, Feijie ;

Liu, Yuanhong .

SYNLETT, 2007, (06) :964-968

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