Chiral Calcium VAPOL Phosphate Mediated Asymmetric Chlorination and Michael Reactions of 3-Substituted Oxindoles

被引：156

作者：

Zheng, Wenhua ^{[1
]}

Zhang, Zuhui ^{[1
]}

Kaplan, Matthew J. ^{[1
]}

Antilla, Jon C. ^{[1
]}

机构：

[1] Univ S Florida, Dept Chem, Tampa, FL 33620 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 10期

基金：

美国国家科学基金会; 美国国家卫生研究院;

关键词：

ENANTIOSELECTIVE FLUORINATION; ALPHA-CHLORINATION; PHOSPHORIC-ACID; ALDOL REACTION; CONSTRUCTION; HALOGENATION; CATALYST; REARRANGEMENT; BROMINATION; EFFICIENT;

D O I：

10.1021/ja109824x

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We disclose a novel high yielding and highly enantioselective chiral calcium VAPOL phosphate-catalyzed chlorination of 3-substituted oxindoles with N-chlorosuccinimide (NCS). The reaction conditions are also shown to be effective for the catalytic enantioselective Michael addition of 3-aryloxindoles to methyl vinyl ketone.

引用

收藏

页码：3339 / 3341

页数：3

相关论文

共 58 条

[1] Strontium-catalyzed highly enantioselective Michael additions of malonates to enones [J].

Agostinho, Magno ;

Kobayashi, Shu .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (08) :2430-2431

[2] Stronger bronsted acids [J].

Akiyama, Takahiko .

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

[3] Enantioselective Robinson-Type Annulation Reaction Catalyzed by Chiral Phosphoric Acids [J].

Akiyama, Takahiko ;

Katoh, Takuya ;

Mori, Keiji .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (23) :4226-4228

[4] 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

[5]

[Anonymous], 1995, BASIC INORGANIC CHEM

[6] 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

[7] 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

[8] Dimeric Quinidine-Catalyzed Enantioselective Aminooxygenation of Oxindoles: An Organocatalytic Approach to 3-Hydroxyoxindole Derivatives [J].

Bui, Tommy ;

Candeias, Nuno R. ;

Barbas, Carlos F., III .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (16) :5574-+

[9] Expanding the Scope of Cinchona Alkaloid-Catalyzed Enantioselective α-Aminations of Oxindoles: A Versatile Approach to Optically Active 3-Amino-2-oxindole Derivatives [J].

Bui, Tommy ;

Borregan, Mar ;

Barbas, Carlos F., III .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (23) :8935-8938

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

Cai, Yunfei ;

Wang, Wentao ;

Shen, Ke ;

Wang, Jun ;

Hu, Xiaolei ;

Lin, Lili ;

Liu, Xiaohua ;

Feng, Xiaoming .

CHEMICAL COMMUNICATIONS, 2010, 46 (08) :1250-1252

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