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

共 47 条

[1] Taming the Friedel-Crafts Reaction: Organocatalytic Approach to Optically Active 2,3-Dihydrobenzofurans [J].

Albrecht, Lukasz ;

Ransborg, Lars Krogager ;

Lauridsen, Vibeke ;

Overgaard, Mette ;

Zweifel, Theo ;

Jorgensen, Karl Anker .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (52) :12496-12500

[2] N-Heterocyclic carbene catalysed 1,6-hydrophosphonylation of p-quinone methides and fuchsones: an atom economical route to unsymmetrical diaryl- and triarylmethyl phosphonates [J].

Arde, Panjab ;

Anand, Ramasamy Vijaya .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (24) :5550-5554

[3]

Barton D., 1999, COMPREHENSIVE NATURA, V3

[4]

Barton D., 1999, Comprehensive Natural Products Chemistry, V1

[5]

Barton D., 1999, COMPREHENSIVE NATURA, V8

[6] Recent Progress in the Synthesis of 2,3-Dihydrobenzofurans [J].

Bertolini, Ferruccio ;

Pineschi, Mauro .

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2009, 41 (05) :385-418

[7]

Buckingham J., 1994, DICT NATURAL PRODUCT

[8]

Carlos J.B., 2016, ACS CATAL, V6, P442

[9] Advances in Organocatalytic 1,6-Addition Reactions: Enantioselective Construction of Remote Stereogenic Centers [J].

Chauhan, Pankaj ;

Kaya, Ugur ;

Enders, Dieter .

ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (06) :888-912

[10] Insecticidal neolignans from Piper decurrens [J].

Chauret, DC ;

Bernard, CB ;

Arnason, JT ;

Durst, T ;

Krishnamurty, HG ;

SanchezVindas, P ;

Moreno, N ;

SanRoman, L ;

Poveda, L .

JOURNAL OF NATURAL PRODUCTS, 1996, 59 (02) :152-155

← 1 2 3 4 5 →