Highly enantioselective α-chlorination of cyclic β-ketoesters catalyzed by N,N′-Dioxide using NCS as the chlorine source

被引：58

作者：

Cai, Yunfei ^{[1
]}

Wang, Wentao ^{[1
]}

Shen, Ke ^{[1
]}

Wang, Jun ^{[1
]}

Hu, Xiaolei ^{[1
]}

Lin, Lili ^{[1
]}

Liu, Xiaohua ^{[1
]}

Feng, Xiaoming ^{[1
]}

机构：

[1] Sichuan Univ, Coll Chem, Key Lab Green Chem & Technol, Minist Educ, Chengdu 610064, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2010年 / 46卷 / 08期

基金：

中国国家自然科学基金;

关键词：

KETO-ESTERS; CHIRAL N; N'-DIOXIDES; ASYMMETRIC CATALYSIS; CINCHONA ALKALOIDS; CARBONYL-COMPOUNDS; STRECKER REACTION; MICHAEL ADDITION; AMMONIUM-SALTS; FLUORINATION; ALDEHYDES;

D O I：

10.1039/b922769e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A simple and highly efficient N,N'-dioxide organocatalyst system was developed for the asymmetric alpha-chlorination of cyclic beta-ketoesters using easily available NCS as the chlorine source to provide a series of optically active alpha-chloro-beta-ketoesters in excellent yields with 90-98% ee.

引用

页码：1250 / 1252

页数：3

共 50 条

[1] Enantioselective Linchpin Catalysis by SOMO Catalysis: An Approach to the Asymmetric α-Chlorination of Aldehydes and Terminal Epoxide Formation [J].

Amatore, Muriel ;

Beeson, Teresa D. ;

Brown, Sean P. ;

MacMillan, David W. C. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) :5121-5124

[2]

[Anonymous], 1992, APPL ORGANOMET CHEM

[3] Organocatalytic asymmetric α-halogenation of 1,3-dicarbonyl compounds [J].

Bartoli, G ;

Bosco, M ;

Carlone, A ;

Locatelli, M ;

Melchiorre, P ;

Sambri, L .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (38) :6219-6222

[4] Enantioselective organocatalytic α-fluorination of aldehydes [J].

Beeson, TD ;

MacMillan, DWC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (24) :8826-8828

[5] Enantioselective chlorination and fluorination of β-keto phosphonates catalyzed by chiral Lewis acids [J].

Bernardi, L ;

Jorgensen, KA .

CHEMICAL COMMUNICATIONS, 2005, (10) :1324-1326

[6] Direct and enantioselective organocatalytic α-chlorination of aldehydes [J].

Brochu, MP ;

Brown, SP ;

MacMillan, DWC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (13) :4108-4109

[7] Design, synthesis, and evaluation of a novel class of enantioselective electrophilic fluorinating agents:: N-fluoro ammonium salts of cinchona alkaloids (F-CA-BF4) [J].

Cahard, D ;

Audouard, C ;

Plaquevent, JC ;

Roques, N .

ORGANIC LETTERS, 2000, 2 (23) :3699-3701

[8] Chiral pyridine N-oxides:: useful ligands for asymmetric catalysis [J].

Chelucci, G ;

Murineddu, G ;

Pinna, GA .

TETRAHEDRON-ASYMMETRY, 2004, 15 (09) :1373-1389

[9]

De Kimpe N., 1990, CHEM ALPHA HALOKETON

[10] Recent developments in catalytic, asymmetric α-halogenation:: A new frontier in asymmetric catalysis [J].

France, S ;

Weatherwax, A ;

Lectka, T .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (03) :475-479

← 1 2 3 4 5 →