Enantioselective [3+2] Formal Cycloaddition of 1-Styrylnaphthols with Quinones Catalyzed by a Chiral Phosphoric Acid

被引：41

作者：

Feng, Wang ^{[1
]}

Yang, Hui ^{[1
]}

Wang, Zhe ^{[1
]}

Gou, Bo-Bo ^{[1
]}

Chen, Jie ^{[1
]}

Zhou, Ling ^{[1
]}

机构：

[1] Northwest Univ, Dept Chem & Mat Sci, Minist Educ, Key Lab Synthet & Nat Funct Mol Chem, Xian 710127, Shaanxi, Peoples R China

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 10期

基金：

中国国家自然科学基金;

关键词：

H INSERTION REACTIONS; LEWIS-ACID; ASYMMETRIC-SYNTHESIS; PROMOTED REACTIONS; BRONSTED ACID; O-HYDROXYSTYRENES; STYRENYL SYSTEMS; POVAROV REACTION; CONSTRUCTION; RESVERATROL;

D O I：

10.1021/acs.orglett.8b00988

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first highly enantioselective [3 + 2] formal cycloaddition of 1-styrylnaphthols (or phenol) with quinones catalyzed by a chiral phosphoric acid has been reported. A class of trans-2,3-diarylbenzofurans were prepared efficiently (up to 99% yield, >20:1 dr, 99% ee). This organocatalytic procedure allows lowering of the catalyst loading to 0.5 mol % without considerable loss in reactivity and enantioselectivity.

引用

页码：2929 / 2933

页数：5

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