Merging Nucleophilic and Hydrogen Bonding Catalysis: An Anion Binding Approach to the Kinetic Resolution of Propargylic Amines

被引：114

作者：

Klauber, Eric G. ^{[1
]}

De, Chandra Kanta ^{[1
]}

Shah, Tejas K. ^{[1
]}

Seidel, Daniel ^{[1
]}

机构：

[1] Rutgers State Univ, Dept Chem & Chem Biol, Piscataway, NJ 08854 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2010年 / 132卷 / 39期

关键词：

BRONSTED ACID; METAL CATALYSIS; CHIRAL ANION; ENANTIOSELECTIVE ADDITION; IMINES; ALKYLATION; ALDEHYDES; ALCOHOLS; ALKYNES; SEARCH;

D O I：

10.1021/ja105337h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient kinetic resolution of primary propargylic amines with s-factors of up to 56 is reported. The strategy is based on a dual catalytic approach, namely the use of a newly developed and easy-to-make thiourea-amide anion binding catalyst in combination with 4-(dimethylamino)pyridine (DMAP), both employed at a 5 mol% catalyst loading. Benzylic amines are also resolved with s-factors of up to 38.

引用

页码：13624 / 13626

页数：3

共 73 条

[1] Stronger bronsted acids [J].

Akiyama, Takahiko .

CHEMICAL REVIEWS, 2007, 107 (12) :5744-5758

[2] Three-component enantioselective synthesis of propargylamines through Zr-catalyzed additions of alkyl zinc reagents to alkynylimines [J].

Akullian, LC ;

Snapper, ML ;

Hoveyda, AH .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (35) :4244-4247

[3] ASYMMETRIC-SYNTHESIS OF ACIDS BY THE PALLADIUM-CATALYZED HYDROCARBOXYLATION OF OLEFINS IN THE PRESENCE OF (R)-(-)-1,1'-BINAPHTHYL-2,2'-DIYL OR (S)-(+)-1,1'-BINAPHTHYL-2,2'-DIYL HYDROGEN PHOSPHATE [J].

ALPER, H ;

HAMEL, N .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (07) :2803-2804

[4]

Arai S, 2001, ANGEW CHEM INT EDIT, V40, P234, DOI 10.1002/1521-3773(20010105)40:1<234::AID-ANIE234>3.0.CO

[5]

2-K

[6] Kinetic resolutions of indolines by a nonenzymatic acylation catalyst [J].

Arp, Forrest O. ;

Fu, Gregory C. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (44) :14264-14265

[7] Highly enantioselective access to primary propargylamines: 4-piperidinone as a convenient protecting group [J].

Aschwanden, Patrick ;

Stephenson, Corey R. J. ;

Carreira, Erick M. .

ORGANIC LETTERS, 2006, 8 (11) :2437-2440

[8] Potassium and silver chiral cobaltate(III) complexes as precatalysts for asymmetric C-C bond formation [J].

Belokon, Yuri N. ;

Maleev, Viktor I. ;

Kataev, Dimitri A. ;

Mal'fanov, Ilya. L. ;

Bulychev, Alexander G. ;

Moskalenko, Margarita A. ;

Saveleva, Tat'yana F. ;

Skrupskaya, Tat'yana V. ;

Lyssenko, Konstantin A. ;

Godovikov, Ivan A. ;

North, Michael .

TETRAHEDRON-ASYMMETRY, 2008, 19 (07) :822-831

[9] Kinetic resolution of propargylic alcohols catalyzed by benzotetramisole [J].

Birman, Vladimir B. ;

Guo, Lei .

ORGANIC LETTERS, 2006, 8 (21) :4859-4861

[10] Kinetic resolution of 2-oxazolidinones via catalytic, enantioselective N-acylation [J].

Birman, Vladimir B. ;

Jiang, Hui ;

Li, Ximin ;

Guo, Lei ;

Uffman, Eric W. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (20) :6536-6537

← 1 2 3 4 5 6 7 8 →