Chemoselective tandem SN2′/SN2′′/inter- or intramolecular Diels-Alder reaction of γ-vinyl MBH carbonates with phenols and o-hydroxychalcones

被引：5

作者：

Liu, Wei ^{[1
]}

Zhang, Le ^{[1
]}

Liu, Ye ^{[1
]}

Fan, Shi-Lu ^{[1
]}

Dai, Jian-Jun ^{[1
]}

Tao, Wei ^{[1
]}

Zhu, Hui-Xia ^{[1
]}

Xiao, Hua ^{[1
,2
]}

机构：

[1] Hefei Univ Technol, Sch Food & Biol Engn, 485 Danxia Rd, Hefei 230601, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synthet Chem Nat Subst, 345 Lingling Lu, Shanghai 200032, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2022年 / 58卷 / 70期

关键词：

ALLYLIC ALKYLATION; HILLMAN; DIMERIZATION; DERIVATIVES; ANNULATION; ACETATES;

D O I：

10.1039/d2cc03771h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An unprecedented consecutive S(N)2 '/S(N)2 '' addition of phenol to gamma-vinyl MBH carbonate forms a reactive diene intermediate, followed by a dimerization/elimination process to give functionalized exocyclohexenes with excellent chemoselectivity. When using o-hydroxychalcones as pronucleophiles, an S(N)2 '/S(N)2 ''/intramolecular Diels-Alder reaction sequence occurs, selectively producing a series of pharmaceutically intriguing tricyclic chromane derivatives with good diastereoselectivity. The good nucleophilicity and fair nucleofugicity exhibited by phenoxy anion play a pivotal role in the S(N)2 '' addition step.

引用

页码：9794 / 9797

页数：4