Water-Promoted Palladium-Catalyzed Asymmetric Ring-Opening of Oxabenzonorbornadienes with Alkoxysilanes

被引：9

作者：

Tan, Yun ^{[1
]}

Yao, Yongqi ^{[1
]}

Yang, Wen ^{[1
]}

Lin, Qifu ^{[1
]}

Huang, Guobao ^{[2
]}

Tan, Minxiong ^{[2
]}

Chen, Shuqi ^{[1
]}

Chen, Donghan ^{[1
]}

Yang, Dingqiao ^{[1
]}

机构：

[1] South China Normal Univ, Coll Chem, Minist Educ, Key Lab Theoret Chem Environm, Guangzhou 510006, Guangdong, Peoples R China

[2] Normal Univ, Coll Chem & Food Sci Yulin, Key Lab Agr Resources Chem & Biotechnol, Yulin 537000, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2020年 / 362卷 / 01期

基金：

中国国家自然科学基金;

关键词：

Water Promotion; Palladium Catalys; Asymmetric Ring-Opening; Oxabenzonorbornadienes; Alkoxysilanes; One-Pot Reaction; HECK-TYPE REACTION; OXABICYCLIC ALKENES; BICYCLIC OLEFINS; OXA(AZA)BICYCLIC ALKENES; HETEROBICYCLIC ALKENES; AZABICYCLIC ALKENES; GRIGNARD; AZABENZONORBORNADIENES; REAGENTS; ACIDS;

D O I：

10.1002/adsc.201901152

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Water-promoted palladium-catalyzed asymmetric ring-opening (ARO) reaction of oxabenzonorbornadienes with a wide variety of alkoxysilanes has been developed in a one-pot fashion, yielding cis-1,2-dihydronaphthalen-1-ols in favourable yields (up to 98%) with gratifying enantioselectivities (up to 98% ee) under mild conditions. To the best of our knowledge, it represents the first example in the ring-opening reactions of oxabicyclic alkenes with alkoxysilanes. Furthermore, the cis-1,2-configuration of product was established by X-ray diffraction analysis, and a possible mechanism for the present catalytic ring-opening reaction was also proposed.

引用

页码：139 / 145

页数：7

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