Unexpected Cascade Reactions of Ortho-Hydroxyenaminones and β,γ-Unsaturated α-Ketoesters to Access Hydrogenated Benzoxazolepolycycles and Pyrrole-Phenol Atropisomers

被引：13

作者：

Bai, Xuguan ^{[1
]}

Wang, Lele ^{[1
]}

Zhang, Ziying ^{[1
]}

Zhang, Kuan ^{[1
]}

Bu, Zhanwei ^{[1
]}

Wu, Yufeng ^{[1
]}

Zhang, Wenjing ^{[2
]}

Wang, Qilin ^{[1
]}

机构：

[1] Henan Univ, Coll Chem & Chem Engn, Inst Funct Organ Mol Engn, Kaifeng 475004, Peoples R China

[2] Zhengzhou Univ, Coll Chem, Zhengzhou 450001, Henan, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2019年 / 361卷 / 21期

基金：

中国国家自然科学基金;

关键词：

cascade reaction; benzoxazole; axial chirality; polycyclic heterocycle; atropisomer; ENANTIOSELECTIVE SYNTHESIS; KETAL SPIROOXINDOLES; ASYMMETRIC-SYNTHESIS; BIOMIMETIC SYNTHESIS; BICYCLIC N; O; CYCLIZATION; DEAROMATIZATION; CONSTRUCTION; CYCLOADDITION; TRYPTOPHOLS;

D O I：

10.1002/adsc.201900950

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

An unexpected BF3.OEt2-catalyzed Michael addition/cyclization/dehydration sequence of ortho-hydroxyenaminones with aromatic or aliphatic aldehyde-derived beta,gamma -unsaturated alpha -ketoesters has been achieved to afford a wide range of fused hydrogenated benzoxazole polycycles in 67-95% yields in a highly diastereoselective manner. When isatin-derived beta,gamma -unsaturated alpha -ketoesters were employed as substrates, completely different reactivities were observed, delivering an array of new atropisomers with an oxindole-substituted N-C axially chiral pyrrole-phenol backbone in up to 97% yield. Moreover, DFT calculations were conducted to account for the possible reaction pathway and the stereochemistry.

引用

页码：4893 / 4901

页数：9

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