Control of N-Heterocyclic Carbene Catalyzed Reactions of Enals: Asymmetric Synthesis of Oxindole-γ-Amino Acid Derivatives

被引：50

作者：

Chen, Xiang-Yu ^{[1
]}

Xiong, Jia-Wen ^{[1
]}

Liu, Qiang ^{[1
]}

Li, Sun ^{[1
]}

Sheng, He ^{[1
]}

von Essen, Carolina ^{[2
]}

Rissanen, Kari ^{[2
]}

Enders, Dieter ^{[1
]}

机构：

[1] Rhein Westfal TH Aachen, Inst Organ Chem, Landoltweg 1, D-52074 Aachen, Germany

[2] Univ Jyvaskyla, Dept Chem, Nanosci Ctr, Jyvaskyla 40014, Finland

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2018年 / 57卷 / 01期

基金：

欧洲研究理事会;

关键词：

asymmetric synthesis; carbenes; cycloaddition; lactams; oxindoles; QUATERNARY STEREOGENIC CENTERS; BOND-FORMING REACTIONS; ONE-POT SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; ALPHA; BETA-UNSATURATED ALDEHYDES; COOPERATIVE CATALYSIS; ANNULATION REACTIONS; HOMOENOLATE ADDITIONS; EFFICIENT SYNTHESIS; SPIRO-HETEROCYCLES;

D O I：

10.1002/anie.201708994

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A strategy to control the switch between a non-cycloaddition reaction and a cycloaddition reaction of enals, using N-heterocyclic carbene (NHC) catalyisis, has been developed. The new scalable protocol leads to gamma-amino-acid esters bearing a tetrasubstituted stereocenter in good yields and high stereoselectivities by homo-Mannich reactions of enals and isatin-derived ketimines. By simply changing the N-ketimine substituent to an ortho-hydroxy phenyl group, the corresponding spirocyclic oxindolo-gamma-lactams are obtained.

引用

页码：300 / 304

页数：5

共 50 条

[31] Rapid Access to Spirocylic Oxindoles: Application of Asymmetric N-Heterocyclic Carbene-Catalyzed [3+3] Cycloaddition of Imines to Oxindole-Derived Enals
Xie, Danbo
Yang, Limin
Lin, Youqiang
Zhang, Zhiming
Chen, Dongdong
Zeng, Xiaofei
Zhong, Guofu
ORGANIC LETTERS, 2015, 17 (10) : 2318 - 2321
[32] N-heterocyclic carbene-catalyzed radical reactions
Kun-Quan Chen
He Sheng
Qiang Liu
Pan-Lin Shao
Xiang-Yu Chen
Science China(Chemistry), 2021, (01) : 7 - 16
[33] N-heterocyclic carbene-catalyzed radical reactions
Chen, Kun-Quan
Sheng, He
Liu, Qiang
Shao, Pan-Lin
Chen, Xiang-Yu
SCIENCE CHINA-CHEMISTRY, 2021, 64 (01) : 7 - 16
[34] N-heterocyclic carbene-catalyzed radical reactions
Kun-Quan Chen
He Sheng
Qiang Liu
Pan-Lin Shao
Xiang-Yu Chen
Science China Chemistry, 2021, 64 : 7 - 16
[35] Synthesis and Reactions of N-Heterocyclic Carbene Boranes
Curran, Dennis P.
Solovyev, Andrey
Brahmi, Malika Makhlouf
Fensterbank, Louis
Malacria, Max
Lacote, Emmanuel
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (44) : 10294 - 10317
[36] N-Heterocyclic Carbene Catalyzed Activation of Esters: A New Option for Asymmetric Domino Reactions
Chauhan, Pankaj
Enders, Dieter
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (06) : 1485 - 1487
[37] Expeditious Synthesis of Functionalized Piperidines by Regioselective Ring Opening of Aziridines by Enals Catalyzed by an N-Heterocyclic Carbene
Singh, Santosh
Rai, Vijai K.
Singh, Pankaj
Yadav, Lal Dhar S.
SYNTHESIS-STUTTGART, 2010, (17): : 2957 - 2964
[38] Asymmetric intermolecular Stetter reactions catalyzed by a novel triazolium derived N-heterocyclic carbene
Enders, Dieter
Han, Jianwei
Henseler, Alexander
CHEMICAL COMMUNICATIONS, 2008, (34) : 3989 - 3991
[39] N-Heterocyclic Carbene/Lewis Acid Strategy for the Stereoselective Synthesis of Spirocyclic Oxindole-Dihydropyranones
Xiao, Zhaoxin
Yu, Chenxia
Li, Tuanjie
Wang, Xiang-Shan
Yao, Changsheng
ORGANIC LETTERS, 2014, 16 (14) : 3632 - 3635
[40] Bifunctional N-Heterocyclic Carbene Catalyzed [3+4] Annulation of Enals and Aurones
Liang, Zhi-Qin
Gao, Zhong-Hua
Jia, Wen-Qiang
Ye, Song
CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (05) : 1868 - 1872

← 1 2 3 4 5 →