Exploiting Distal Reactivity of Coumarins: A Rhodium-Catalyzed Vinylogous Asymmetric Ring-Opening Reaction

被引：44

作者：

Loh, Charles C. J. ^{[1
]}

Schmid, Matthias ^{[1
]}

Peters, Brendan ^{[1
]}

Fang, Xiang ^{[1
,2
,3
]}

Lautens, Mark ^{[1
]}

机构：

[1] Univ Toronto, Dept Chem, Davenport Chem Labs, 80 St George St, Toronto, ON M5S 3H6, Canada

[2] E China Univ Sci & Technol, Sch Chem & Mol Engn, Adv Mat Lab, 130 Meilong Rd, Shanghai 200237, Peoples R China

[3] E China Univ Sci & Technol, Sch Chem & Mol Engn, Inst Fine Chem, 130 Meilong Rd, Shanghai 200237, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 14期

基金：

加拿大自然科学与工程研究理事会; 中国国家自然科学基金;

关键词：

enantioselectivity; heterocycles; ring-opening reactions; rhodium; synthetic methods; SILYL KETENE ACETALS; MICHAEL ADDITION; OXABICYCLIC ALKENES; ALPHA; BETA-UNSATURATED ALDEHYDES; PROPARGYLIC ALCOHOLS; MANNICH REACTIONS; BICYCLIC ALKENES; GAMMA-ARYLATION; ALDOL REACTION; OXABENZONORBORNADIENES;

D O I：

10.1002/anie.201600654

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

While the utility of vinylogous enolates is well established in the setting of vinylogous aldol, Mannich, and Michael chemistries, literature reports concerning -reactivity are scarce for other reaction classes. Presented herein is an unprecedented example of vinylogous reactivity exemplified by the rhodium-catalyzed asymmetric ring-opening reaction of oxabicycles. This strategy also provides a powerful route to incorporate the biologically useful coumarin motif into the hydronapthalene scaffold.

引用

页码：4600 / 4604

页数：5

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