Asymmetric organocatalytic synthesis of chiral 3,3-disubstituted oxindoles via a 1,6-conjugate addition reaction

被引：23

作者：

Rahman, Abdul ^{[1
]}

Zhou, Qiaoxia ^{[1
]}

Lin, Xufeng ^{[1
]}

机构：

[1] Zhejiang Univ, Dept Chem, Lab Asymmetr Catalysis & Synth, Hangzhou 310027, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2018年 / 16卷 / 29期

基金：

中国国家自然科学基金;

关键词：

PARA-QUINONE METHIDES; SPINOL-PHOSPHORIC ACIDS; TRIFLUOROMETHYLATED QUATERNARY STEREOCENTERS; TETRAHYDRO-BETA-CARBOLINES; FRIEDEL-CRAFTS ALKYLATION; BRONSTED ACID; ENANTIOSELECTIVE SYNTHESIS; STEREOGENIC CENTERS; AROMATIC-ALDEHYDES; EXPEDIENT ACCESS;

D O I：

10.1039/c8ob01169a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly efficient synthesis of chiral 3,3-disubstituted oxindoles was developed using a chiral spirocyclic phosphoric acid catalyzed 1,6-conjugate addition reaction of para-quinone methides derived from N-unprotected isatins with indoles. The reaction proceeds under mild reaction conditions to provide indole-containing N-unprotected oxindoles bearing quaternary stereocenters in good yields and with moderate to excellent enantioselectivities (up to 97% ee).

引用

页码：5301 / 5309

页数：9

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