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
收藏
页码：5301 / 5309
页数：9
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