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
收藏
页码：9003 / 9007
页数：5
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