Catalytic Asymmetric Sulfenylation of Unprotected 3-Substituted Oxindoles

被引：96

作者：

Cai, Yunfei ^{[1
]}

Li, Jun ^{[1
]}

Chen, Weiliang ^{[1
]}

Xie, Mingsheng ^{[1
]}

Liu, Xiaohua ^{[1
]}

Lin, Lili ^{[1
]}

Feng, Xiaoming ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 11期

基金：

中国国家自然科学基金;

关键词：

C-H; FLUORINATION; COMPLEXES;

D O I：

10.1021/ol3009446

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Catalytic asymmetric sulfenylation of unprotected 3-substituted oxindoles has been developed via cooperative catalysis of a chiral N,N-dioxide-Sc(OTf)(3) complex and a Bronsted base. Utilizing readily available N-(phenylthio)phthalimide as the sulfur source, a wide range of optically active 3-phenylthiooxindoles were obtained in excellent yields with excellent enantioselectivities under mild reaction conditions.

引用

收藏

页码：2726 / 2729

页数：4

相关论文

共 50 条

[21] Enantioselective Friedel-Crafts Alkylation of Indoles with Alkylidene Malonates Catalyzed by N,N′-Dioxide-Scandium(III) Complexes: Asymmetric Synthesis of β-Carbolines [J].

Liu, Yanling ;

Shang, Deju ;

Zhou, Xin ;

Liu, Xiaohua ;

Feng, Xiaoming .

CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (09) :2055-2058

[22] Organocatalytic Asymmetric Synthesis of Substituted 3-Hydroxy-2-oxindoles via Morita-Baylis-Hillman Reaction [J].

Liu, Yun-Lin ;

Wang, Bo-Lun ;

Cao, Jun-Jie ;

Chen, Long ;

Zhang, Yong-Xue ;

Wang, Chao ;

Zhou, Jian .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (43) :15176-15178

[23] Chiral N-oxides in asymmetric catalysis [J].

Malkov, Andrei V. ;

Kocovsky, Pavel .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (01) :29-36

[24] Enantioselective organocatalyzed a sulfenylation of aldehydes [J].

Marigo, M ;

Wabnitz, TC ;

Fielenbach, D ;

Jorgensen, KA .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (05) :794-797

[25] Construction of spiro[pyrrolidine-3,3′-oxindoles] -: Recent applications to the synthesis of oxindole alkaloids [J].

Marti, C ;

Carreira, EM .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (12) :2209-2219

[26]

Mikami K, 2002, ANGEW CHEM INT EDIT, V41, P3555, DOI 10.1002/1521-3773(20021004)41:19<3554::AID-ANIE3554>3.0.CO

[27]

2-P

[28] Catalytic Asymmetric Synthesis of 3-Aminooxindoles: Enantiofacial Selectivity Switch in Bimetallic vs Monometallic Schiff Base Catalysis [J].

Mouri, Shinsuke ;

Chen, Zhihua ;

Mitsunuma, Harunobu ;

Furutachi, Makoto ;

Matsunaga, Shigeki ;

Shibasaki, Masakatsu .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (04) :1255-+

[29] Metal-organic cooperative catalysis in C-H and C-C bond activation and its concurrent recovery [J].

Park, Young Jun ;

Park, Jung-Woo ;

Jun, Chul-Ho .

ACCOUNTS OF CHEMICAL RESEARCH, 2008, 41 (02) :222-234

[30] Asymmetric construction of quaternary stereocenters by direct organocatalytic amination of 3-substituted oxindoles [J].

Qian, Zi-Qing ;

Zhou, Feng ;

Du, Tai-Ping ;

Wang, Bo-Lun ;

Ding, Miao ;

Zhao, Xiao-Li ;

Zhou, Jian .

CHEMICAL COMMUNICATIONS, 2009, (44) :6753-6755

← 1 2 3 4 5 →