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
收藏
页码：1681 / 1688
页数：8
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