STUDIES TOWARDS THE N-ACYLATIVE KINETIC RESOLUTION OF NOBIN

被引：16

作者：

Arseniyadis, Stellios ^{[1
]}

Mahesh, Mohan ^{[1
]}

McDaid, Paul ^{[1
]}

Hampel, Thomas ^{[1
]}

Davey, Stephen G. ^{[1
]}

Spivey, Alan C. ^{[1
]}

机构：

[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England

来源：

COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS | 2011年 / 76卷 / 10期

基金：

英国工程与自然科学研究理事会;

关键词：

Kinetic resolution; Atropisomerism; Asymmetric synthesis; Organocatalysis; NUCLEOPHILIC AROMATIC-SUBSTITUTION; 2-COMPONENT MOLECULAR-CRYSTAL; 1-NAPHTHYL GRIGNARD-REAGENTS; ENANTIOSELECTIVE ACYLATION; ASYMMETRIC CATALYSIS; FACILE SYNTHESIS; DERIVATIVES; 2-AMINO-2'-HYDROXY-1,1'-BINAPHTHYL; 2-NAPHTHOL; EFFICIENT;

D O I：

10.1135/cccc2011034

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An investigation into the N-acylation of atropisomeric anilines 8 and 2, which are related to NOBIN (1), catalysed by small molecule chiral pyridine-based nucleophilic catalysts is described. The first organocatalytic kinetic resolution (KR) of an atropisomeric aniline is described.

引用

页码：1239 / 1253

页数：15

共 55 条

[1] Catalytic and stoichiometric approaches to the desymmetrisation of centrosymmetric piperazines by enantioselective acylation: a total synthesis of Dragmacidin A [J].

Anstiss, Mark ;

Nelson, Adam .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (22) :4135-4143

[2] Kinetic resolution of 1,1′-binaphthylamines via lipase-catalyzed amidation [J].

Aoyagi, N ;

Izumi, T .

TETRAHEDRON LETTERS, 2002, 43 (32) :5529-5531

[3]

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

[4]

2-K

[5] 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

[6] 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

[7] Update 1 of: BINOL: A Versatile Chiral Reagent [J].

Brunel, Jean Michel .

CHEMICAL REVIEWS, 2007, 107 (09) :PR1-PR45

[8]

Brunner H, 2003, Z NATURFORSCH B, V58, P821

[9] Enantioselective catalysis.: Part 143:: Astonishingly high enantioselectivity in the transfer hydrogenation of acetophenone with 2-propanol using Ru complexes of the Schiff base derived from (S)-2-amino-2-hydroxy-1,1′-binaphthyl (NOBIN) and 2-pyridinecarbaldehyde [J].

Brunner, H ;

Henning, F ;

Weber, M .

TETRAHEDRON-ASYMMETRY, 2002, 13 (01) :37-42

[10] Merging Nucleophilic and Hydrogen Bonding Catalysis: An Anion Binding Approach to the Kinetic Resolution of Amines [J].

De, Chandra Kanta ;

Klauber, Eric G. ;

Seidel, Daniel .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (47) :17060-+

← 1 2 3 4 5 6 →