Catalyst-free synthesis of 2,3-dihydrobenzofurans through [4+1] cycloaddition of ortho-hydroxyphenylsubstituted para-quinone methides and sulfur ylides

被引：36

作者：

Chen, Xin-Meng ^{[1
,3
]}

Xie, Ke-Xin ^{[2
]}

Yue, Deng-Feng ^{[1
,3
]}

Zhang, Xiao-Mei ^{[1
]}

Xu, Xiao-Ying ^{[1
]}

Yuan, Wei-Cheng ^{[1
]}

机构：

[1] Chinese Acad Sci, Chengdu Inst Organ Chem, Natl Engn Res Ctr Chiral Drugs, Chengdu 610041, Sichuan, Peoples R China

[2] Chinese Acad Sci, Chengdu Inst Biol, Chengdu 610041, Sichuan, Peoples R China

[3] Univ Chinese Acad Sci, Beijing 100049, Peoples R China

来源：

TETRAHEDRON | 2018年 / 74卷 / 05期

基金：

中国国家自然科学基金;

关键词：

para-Quinone methides; Sulfur yildes; 2,3-Dihydrobenzofurans; Catalyst-free; Cycloaddition; ASYMMETRIC-SYNTHESIS; ENANTIOSELECTIVE CONSTRUCTION; 3-ISOTHIOCYANATO OXINDOLES; POLYCYCLIC SPIROOXINDOLES; LITHOSPERMUM-RUDERALE; POLYPHENOLIC ACIDS; CASCADE REACTION; ANNULATION; NEOLIGNANS; TRIARYLMETHANES;

D O I：

10.1016/j.tet.2017.12.038

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient [4+1] cycloaddition of ortho-hydroxyphenylsubstituted para-quinone methides, and sulfur ylides was achieved under the catalyst-free condition. With this developed protocol, a series of trans-2,3-dihydrobenzofurans were obtained in excellent yields (up to 99%) with high diastereoselectivities (>20:1 dr). The usefulness of the protocol was also demonstrated by the versatile conversions of the 2,3-dihydrobenzofurans into other functionalized benzofurans. (C) 2017 Elsevier Ltd. All rights reserved.

引用

页码：600 / 605

页数：6

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