NHC-Catalyzed Enantioselective [4+3] Cycloaddition of Ortho-Hydroxyphenyl Substituted Para-Quinone Methides with Isatin-Derived Enals

被引：113

作者：

Li, Wenjun ^{[1
]}

Yuan, Huijun ^{[1
]}

Liu, Zhantao ^{[1
]}

Zhang, Zhongyin ^{[1
]}

Cheng, Yuyu ^{[2
]}

Li, Pengfei ^{[2
]}

机构：

[1] Qingdao Univ, Sch Pharm, Dept Med Chem, Qingdao 266021, Shandong, Peoples R China

[2] Southern Univ Sci & Technol, Dept Chem, Shenzhen 518055, Guangdong, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2018年 / 360卷 / 13期

基金：

中国国家自然科学基金;

关键词：

Cycloaddition; Enal; NHC; p-QMs; Spirobenzoxopinones; BETA-ALKYNYL KETONES; DIELS-ALDER REACTION; 3+4 ANNULATION; ASYMMETRIC-SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; AZOMETHINE IMINES; EPSILON-LACTONES; ACCESS; CONSTRUCTION; STRATEGY;

D O I：

10.1002/adsc.201800337

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The first enantioselective cycloaddition of ortho-hydroxyphenyl substituted para-quinone methides has been established by employing isatin-derived enals as suitable 3C-synthons under chiral N-heterocyclic carbene catalysis. By using this strategy, biologically important E-lactones have been prepared in good yields (up to 89%) and excellent asymmetric inductions (up to >99%ee, >20:1dr). Notably, this methodology opens a direct [4+3] annulation entry for the asymmetric synthesis of spirobenzoxopinones bearing an oxindole moiety connected through the spirocenter.

引用

页码：2460 / 2464

页数：5

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