Enantioselective Organocatalytic Three-Component Vinylogous Michael/Aldol Tandem Reaction among 3-Alkylidene oxindoles, Methyleneindolinones, and Aldehydes

被引：6

作者：

Xu, Jing-Xiang ^{[1
]}

Jiang, Yi-Syun ^{[1
]}

Chen, Chih-Hao ^{[2
]}

Sathishkumar, Nadaraj ^{[2
]}

Chu, Kai-Ti ^{[3
]}

Chiang, Ming-Hsi ^{[3
]}

Chen, Hsin-Tsung ^{[2
]}

Han, Jeng-Liang ^{[1
]}

机构：

[1] Natl Chung Hsing Univ, Dept Chem, Taichung 40227, Taiwan

[2] Chung Yuan Christian Univ, Dept Chem, Taoyuan 32023, Taiwan

[3] Acad Sinica, Inst Chem, Taipei 11529, Taiwan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 87卷 / 01期

关键词：

DIELS-ALDER; QUATERNARY STEREOCENTERS; ASYMMETRIC-SYNTHESIS; 3-ALKENYL-2-SILYLOXYINDOLES; HYDROXYMETHYLATION; SPIROOXINDOLES; TRIENAMINES; DIASTEREO; ACCESS;

D O I：

10.1021/acs.joc.1c02180

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We reported a one-pot enantioselective three-component vinylogous Michael/aldol tandem reaction of prochiral 3-alkylidene oxindoles with methyleneindolinones and aldehydes using bifunctional organocatalysts. A variety of enantioenriched 3,3-disubstituted oxindoles 3 and spirolactones 4 were generated in moderate yields (up to 78%) with high stereoselectivities (up to >20:1 dr, >99% ee). Intriguingly, we observed that the aldol reaction with paraformaldehyde generates 3,3-disubstituted oxindoles 3 bearing a hydroxymethyl group, while the reaction with aliphatic aldehydes generates spirolactones 4.

引用

页码：197 / 210

页数：14