Organocatalytic Michael addition of unprotected 3-substituted oxindoles to nitroolefins

被引：70

作者：

Ding, Miao ^{[1
]}

Zhou, Feng ^{[1
]}

Qian, Zi-Qing ^{[1
]}

Zhou, Jian ^{[1
]}

机构：

[1] E China Normal Univ, Shanghai Key Lab Green Chem & Chem Proc, Dept Chem, Shanghai 200062, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2010年 / 8卷 / 13期

关键词：

FRIEDEL-CRAFTS ALKYLATION; CATALYTIC ASYMMETRIC-SYNTHESIS; QUATERNARY STEREOGENIC CENTERS; ENANTIOSELECTIVE SYNTHESIS; CONJUGATE ADDITION; CARBENE LIGANDS; ALPHA-ARYLATION; THIOUREA; NITROALKENES; CONSTRUCTION;

D O I：

10.1039/c004037a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Quinidine was found to catalyze the Michael addition of unprotected 3-substituted oxindoles to nitroolefins in excellent yield and moderate to good diastereoselectivity. Bifunctional quinidine derived thiourea catalyst 10 could catalyze this reaction to afford the major diastereomer in up to 85% ee.

引用

页码：2912 / 2914

页数：3

共 50 条

[1] Organocatalytic Michael addition of unprotected 3-substituted oxindoles to nitroolefins (vol 8, pg 2912, 2010)
Ding, Miao
Zhou, Feng
Qian, Zi-Qing
Zhou, Jian
ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (24) : 5700 - 5700
[2] Organocatalytic asymmetric Michael addition of unprotected 3-substituted oxindoles to 1,4-naphthoquinone
Yu, Jin-Sheng
Zhou, Feng
Liu, Yun-Lin
Zhou, Jian
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2012, 8 : 1360 - 1365
[3] Enantioselective organocatalytic oxyamination of unprotected 3-substituted oxindoles
Companyo, Xavier
Valero, Guillem
Pineda, Oriol
Calvet, Teresa
Font-Bardia, Merce
Moyano, Albert
Rios, Ramon
ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (02) : 431 - 439
[4] Cinchona alkaloid-based phosphoramide catalyzed highly enantioselective Michael addition of unprotected 3-substituted oxindoles to nitroolefins
Ding, Miao
Zhou, Feng
Liu, Yun-Lin
Wang, Cui-Hong
Zhao, Xiao-Li
Zhou, Jian
CHEMICAL SCIENCE, 2011, 2 (10) : 2035 - 2039
[5] Asymmetric Michael Addition Reaction of 3-Substituted Oxindoles to Nitroolefins Catalyzed by a Chiral Alkyl-Substituted Thiourea Catalyst
Li, Xin
Zhang, Bo
Xi, Zhi-Guo
Luo, Sanzhong
Cheng, Jin-Pei
ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (2-3) : 416 - 424
[6] Organocatalytic asymmetric Michael addition of 3-substituted oxindoles to α,β-unsaturated acyl phosphonates for the synthesis of 3,3′-disubstituted oxindoles with chiral squaramides
Chen, Lin
You, Yong
Zhang, Ming-Liang
Zhao, Jian-qiang
Zuo, Jian
Zhang, Xiao-Mei
Yuan, Wei-Cheng
Xu, Xiao-Ying
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (15) : 4413 - 4417
[7] Organocatalytic enantioselective tandem Michael addition-oxidation of 3-substituted oxindoles with 1,4-benzoquinone
Zhang, Yonghong
Hu, Xiaoyan
Li, Shuaishuai
Liao, Yijun
Yuan, Weicheng
Zhang, Xiaomei
TETRAHEDRON, 2014, 70 (11) : 2020 - 2026
[8] Catalytic Asymmetric Sulfenylation of Unprotected 3-Substituted Oxindoles
Cai, Yunfei
Li, Jun
Chen, Weiliang
Xie, Mingsheng
Liu, Xiaohua
Lin, Lili
Feng, Xiaoming
ORGANIC LETTERS, 2012, 14 (11) : 2726 - 2729
[9] Organocatalytic stereoselective Mannich reaction of 3-substituted oxindoles
Tian, Xu
Jiang, Kun
Peng, Jing
Du, Wei
Chen, Ying-Chun
ORGANIC LETTERS, 2008, 10 (16) : 3583 - 3586
[10] Novel tartrate-derived guanidine-catalyzed highly enantio- and diastereoselective Michael addition of 3-substituted oxindoles to nitroolefins
Zou, Liwei
Bao, Xiaoze
Ma, Yuanyuan
Song, Yuming
Qu, Jingping
Wang, Baomin
CHEMICAL COMMUNICATIONS, 2014, 50 (43) : 5760 - 5762

← 1 2 3 4 5 →