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

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