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

被引：35
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
收藏
页码：600 / 605
页数：6
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