Palladium/Zinc Co-Catalyzed syn-Stereoselectively Asymmetric Ring-Opening Reaction of Oxabenzonorbornadienes with Phenols

被引：41

作者：

Li, Sifeng ^{[2
]}

Xu, Jianbin ^{[1
]}

Fan, Baomin ^{[1
,4
]}

Lu, Zhiwu ^{[1
]}

Zeng, Chaoyuan ^{[1
]}

Bian, Zhaoxiang ^{[3
]}

Zhou, Yongyun ^{[1
]}

Wang, Jun ^{[2
]}

机构：

[1] Yunnan Minzu Univ, YMU HKBU Joint Lab Tradit Nat Med, Kunming 650500, Peoples R China

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

[3] Hong Kong Baptist Univ, Sch Chinese Med, Hong Kong, Hong Kong, Peoples R China

[4] Nankai Univ, State Key Lab Elementoorgan Chem, Tinajim 300071, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2015年 / 21卷 / 25期

关键词：

asymmetric catalysis; oxabenzonorbornadienes; phenols; ring-opening reaction; syn-stereoselectivity; OXABICYCLIC ALKENES; ARYLBORONIC ACIDS; BORONIC ACIDS; GRIGNARD; NAPHTHALENE; LIGANDS; CIS-1,2-DIHYDROXY-1,2-DIHYDRONAPHTHALENE; ENANTIOSELECTIVITY; ISOMERIZATION; METABOLITES;

D O I：

10.1002/chem.201500816

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new palladium/zinc co-catalyst system associated with chiral (R)-Difluorphos for asymmetric ring-opening reaction of oxabenzonorbornadienes with phenols is reported. This catalyst system allows the formation of cis-2-aryloxy-1,2-dihydronaphthalen-1-ol products in good yields (up to 95% yield) with excellent enantioselectivities (up to 99% ee). The cis-configuration of the product has been confirmed by X-ray crystal structure analysis. To the best of our knowledge, it represents the first example in ring-opening reactions of bicycloalkenes with heteronucleophiles in a syn-stereoselective manner.

引用

页码：9003 / 9007

页数：5

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