Merging Chiral Bronsted Acid/Base Catalysis: An Enantioselective [4+2] Cycloaddition of o-Hydroxystyrenes with Azlactones

被引：101

作者：

Zhang, Yu-Chen

Zhu, Qu-Ning

Yang, Xue

Zhou, Lu-Jia

Shi, Feng ^{[1
]}

机构：

[1] Jiangsu Normal Univ, Sch Chem & Chem Engn, Xuzhou 221116, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 04期

关键词：

ORTHO-QUINONE METHIDES; DIELS-ALDER REACTION; ASYMMETRIC-SYNTHESIS; BICYCLIC GUANIDINE; POVAROV REACTION; ACID; METAL; CONSTRUCTION; ACTIVATION; ANNULATION;

D O I：

10.1021/acs.joc.6b00078

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An enantioselective [4 + 2] cycloaddition of o-hydroxylstyrenes with azlactones has been established by merging chiral Bronsted acid (chiral phosphoric acid) and base (chiral guanidine) catalysis, which constructed a biologically important dihydrocoumarin scaffold in an efficient and enantioselective style (up to 99% yield, 96:4 er). This approach has not only realized the successful application of o-hydroxylstyrenes as oxa-diene precursors in catalytic asymmetric cycloadditions but also established a new cooperative catalytic system of chiral phosphoric acid and chiral guanidine.

引用

页码：1681 / 1688

页数：8

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