Palladium-Catalyzed syn-Stereocontrolled Ring-Opening of Oxabicyclic Alkenes with Sodium Arylsulfinates

被引：25

作者：

Li, Yue ^{[1
]}

Yang, Wen ^{[1
]}

Cheng, Guo ^{[1
]}

Yang, Dingqiao ^{[1
]}

机构：

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 11期

基金：

中国国家自然科学基金;

关键词：

CROSS-COUPLING REACTION; AZABICYCLIC ALKENES; BICYCLIC OLEFINS; 2-SUBSTITUTED 1,2-DIHYDRO-1-NAPHTHOLS; DIRECT SULFONYLATION; ARYLBORONIC ACIDS; BORONIC ACIDS; OXABENZONORBORNADIENES; ARYL; ARYLATION;

D O I：

10.1021/acs.joc.6b00667

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Palladium-catalyzed syn-stereocontrolled ring opening reactions of oxabenzonorbornadienes with a wide range of sodium arylsulfinates were investigated, affording the desired products in good to excellent yields under an air atmosphere. This protocol provides a low-cost new viable and convenient method toward the synthesis of cis-2-aryl-1,2-dihydronaphthalen-1-ol with good functional group tolerance. In addition, the cis configuration of 3da was established by X-ray diffraction analysis, and a plausible mechanism, for the ring opening reaction was proposed.

引用

页码：4744 / 4750

页数：7

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