1,6-Conjugated addition-mediated [4+1] annulation: an approach to 2,3-dihydrobenzofurans

被引：91
作者：
Liu, Lina [1 ,2 ]
Yuan, Zhenbo [1 ,2 ]
Pan, Rui [1 ,2 ]
Zeng, Yuye [1 ,2 ]
Lin, Aijun [1 ,2 ]
Yao, Hequan [1 ,2 ]
Huang, Yue [3 ]
机构：
[1] China Pharmaceut Univ, Sch Pharm, SKLNM, Nanjing 210009, Jiangsu, Peoples R China
[2] China Pharmaceut Univ, Sch Pharm, Dept Med Chem, Nanjing 210009, Jiangsu, Peoples R China
[3] China Pharmaceut Univ, Sch Sci, Dept Organ Chem, Nanjing 210009, Jiangsu, Peoples R China
来源：
ORGANIC CHEMISTRY FRONTIERS | 2018年 / 5卷 / 04期
基金：
中国国家自然科学基金;
关键词：
PARA-QUINONE METHIDES; BIOACTIVE BENZOFURAN DERIVATIVES; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; AMMONIUM YLIDES; SULFONIUM SALTS; STEREOGENIC CENTERS; FACILE SYNTHESIS; ACID-ESTERS; ADDITION/AROMATIZATION;
D O I：
10.1039/c7qo00846e
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A formal 1,6-conjugated addition-mediated [4 + 1] annulation of ortho-hydroxyphenyl-substituted paraquinone methides with sulfonium or ammonium bromides has been described. This domino-type process offered an efficient method for the synthesis of 2,3-dihydrobenzofurans in good yields, exhibiting good functional group tolerance, scalability and high diastereoselectivity.
引用
收藏
页码：623 / 628
页数：6
相关论文
共 57 条
[1]   New route to herbertanes via a Suzuki cross-coupling reaction:: synthesis of herbertenediol [J].
Abad, A ;
Agulló, C ;
Cuñat, AC ;
Jiménez, D ;
Perni, RH .
TETRAHEDRON, 2001, 57 (48) :9727-9735
[2]   Intramolecular carbolithiation of allyl o-lithioaryl ethers:: A new enantioselective synthesis of functionalized 2,3-dihydrobenzofurans [J].
Barluenga, J ;
Fañanás, FJ ;
Sanz, R ;
Marcos, C .
CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (18) :5397-5407
[3]   A New Organocatalytic Concept for Asymmetric α-Alkylation of Aldehydes [J].
Caruana, Lorenzo ;
Kniep, Florian ;
Johansen, Tore Kiilerich ;
Poulsen, Pernille H. ;
Jorgensen, Karl Anker .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (45) :15929-15932
[4]   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
[5]   A mild method for generation of o-quinone methides under basic conditions. The facile synthesis of trans-2,3-dihydrobenzofurans [J].
Chen, Mu-Wang ;
Cao, Liang-Liang ;
Ye, Zhi-Shi ;
Jiang, Guo-Fang ;
Zhou, Yong-Gui .
CHEMICAL COMMUNICATIONS, 2013, 49 (16) :1660-1662
[6]   Formal [4+1] cycloaddition of camphor-derived sulfonium salts with aldimines: enantioselective synthesis of 2,3-dihydrobenzofurans [J].
Cheng, Ying ;
Hu, Xiao-Qiang ;
Gao, Shuang ;
Lu, Liang-Qiu ;
Chen, Jia-Rong ;
Xiao, Wen-Jing .
TETRAHEDRON, 2013, 69 (19) :3810-3816
[7]   Asymmetric Catalytic 1,6-Conjugate Addition/Aromatization of para-Quinone Methides: Enantioselective Introduction of Functionalized Diarylmethine Stereogenic Centers [J].
Chu, Wen-Dao ;
Zhang, Le-Fen ;
Bao, Xu ;
Zhao, Xian-He ;
Zeng, Chao ;
Du, Ji-Yuan ;
Zhang, Guo-Biao ;
Wang, Fang-Xin ;
Ma, Xiao-Yan ;
Fan, Chun-An .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (35) :9229-9233
[8]   Bifunctional tertiary amine-squaramide catalyzed asymmetric catalytic 1,6-conjugate addition/aromatization of para-quinone methides with oxindoles [J].
Deng, Yu-Hua ;
Zhang, Xiang-Zhi ;
Yu, Ke-Yin ;
Yan, Xu ;
Du, Ji-Yuan ;
Huang, Hanmin ;
Fan, Chun-An .
CHEMICAL COMMUNICATIONS, 2016, 52 (22) :4183-4186
[9]   Asymmetric organocatalytic domino reactions [J].
Enders, Dieter ;
Grondal, Christoph ;
Huettl, Matthias R. M. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (10) :1570-1581
[10]   Synthesis of spiro[2.5]octa-4,7-dien-6-one with consecutive quaternary centers via 1,6-conjugate addition induced dearomatization of para-quinone methides [J].
Gai, Kuo ;
Fang, Xinxin ;
Li, Xuanyi ;
Xu, Jinyi ;
Wu, Xiaoming ;
Lin, Aijun ;
Yao, Hequan .
CHEMICAL COMMUNICATIONS, 2015, 51 (87) :15831-15834
123456