Platinum(II)-Catalyzed Asymmetric Ring-Opening Addition of Arylboronic Acids to Oxabenzonorbornadienes

被引：38

作者：

Pan, Xuejing ^{[1
]}

Huang, Guobao ^{[1
]}

Long, Yuhua ^{[1
]}

Zuo, Xiongjun ^{[1
]}

Xu, Xuan ^{[1
]}

Gu, Fenglong ^{[1
]}

Yang, Dingqiao ^{[1
]}

机构：

[1] S China Normal Univ, Sch Chem & Environm, Minist Educ, Key Lab Theoret Chem Environm, Guangzhou 510006, Guangdong, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 01期

基金：

中国国家自然科学基金;

关键词：

N-BOC-AZABENZONORBORNADIENE; NICKEL-CATALYZED ADDITION; OXABICYCLIC ALKENES; AZABICYCLIC ALKENES; GRIGNARD-REAGENTS; AMINE NUCLEOPHILES; BICYCLIC OLEFINS; COUPLING REACTIONS; BORONIC ACIDS; PALLADIUM;

D O I：

10.1021/jo402386k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new platinum(II)-catalyzed asymmetric ring-opening addition of arylboronic acids to oxabenzonorbornadienes was developed, which afforded the corresponding cis-2-aryl-1,2-dihydronaphthalen-1-ol products in high yields (up to 97%) with moderate to good enantioselectivities (up to 89% ee) under very mild conditions. The effects of various ligands, catalyst loading, bases, solvents, and temperatures on the yield and enantioselectivity of the reaction were also investigated. The cis configuration of product 2m was confirmed by X-ray diffraction analysis. A potential mechanism for the present catalytic reaction is proposed.

引用

页码：187 / 196

页数：10

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