Direct Sulfide-Catalyzed Diastereoselective [4+1] Annulations of ortho-Quinone Methides and Bromides

被引：23

作者：

Liu, Yan-Qing ^{[1
]}

Li, Qing-Zhu ^{[2
]}

Zhu, Hong-Ping ^{[1
,2
]}

Feng, Xin ^{[2
]}

Peng, Cheng ^{[1
]}

Huang, Wei ^{[1
]}

Li, Jun-Long ^{[2
]}

Han, Bo ^{[1
]}

机构：

[1] Chengdu Univ Tradit Chinese Med, State Key Lab Breeding Base Systemat Res Dev & Ut, Chengdu 611137, Sichuan, Peoples R China

[2] Chengdu Univ, Sichuan Ind Inst Antibiot, Antibiot Res & Reevaluat Key Lab Sichuan Prov, Chengdu 610052, Sichuan, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 20期

关键词：

DIARYLPROLINOL SILYL ETHERS; SULFUR YLIDES; ASYMMETRIC-SYNTHESIS; ORGANIC-SYNTHESIS; CYCLIZATION REACTIONS; CARBONYL-COMPOUNDS; HOMO ACTIVATION; ATOM ECONOMY; 2,3-DIHYDROBENZOFURANS; CYCLOADDITION;

D O I：

10.1021/acs.joc.8b02189

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Direct sulfide organocatalysis is an emerging topic in research on synthetic chemistry. Here, an unprecedented sulfide-catalyzed diastereoselective [4+1] annulation of (in situ generated) ortho-quinone methides and bromides is reported. Notably, the robustness of such sulfide organocatalysis was demonstrated by performing the catalytic reaction under oxidative conditions without significantly affecting the reaction outcome. Various dihydrobenzofurans with diverse substituents were obtained with high isolated yields of up to 98% and remarkable diastereoselectivity (>19:1 dr in general).

引用

页码：12753 / 12762

页数：10

共 50 条

[1] Diastereoselective synthesis of spiro-cyclopropanyl-cyclohexadienones via direct sulfide-catalyzed [2+1] annulation of para-quinone methides with bromides
Su, Yingpeng
Zhao, Yanan
Chang, Bingbing
Ling, Qinqin
Feng, Yawei
Zhao, Xiaolong
Huang, Danfeng
Wang, Ke-Hu
Huo, Congde
Hu, Yulai
ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (22) : 4257 - 4266
[2] Phosphine-mediated enantioselective [4+1] annulations between ortho-quinone methides and Morita-Baylis-Hillman carbonates
Cheng, Yuyu
Fang, Zhiqiang
Li, Wenjun
Li, Pengfei
ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (18): : 2728 - 2733
[3] Catalytic Asymmetric [4+1] Cyclization of ortho-Quinone Methides with 3-Chlorooxindoles
Jiang, Xiao-Li
Liu, Si-Jia
Gu, Yu-Qi
Mei, Guang-Jian
Shi, Feng
ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (19) : 3341 - 3346
[4] Enantioselective [4+1] cycloaddition of ortho-quinone methides and bromomalonates under phase-transfer catalysis
Lian, Xiao-Lei
Adili, Alafate
Liu, Bin
Tao, Zhong-Lin
Han, Zhi-Yong
ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (17) : 3670 - 3673
[5] Asymmetric Phosphine-Catalyzed [4+1] Annulations of o-Quinone Methides with MBH Carbonates
Zhou, Tao
Xia, Tong
Liu, Zhenli
Liu, Lu
Zhang, Junliang
ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (23) : 4475 - 4479
[6] Organocatalytic Diastereoselective Dearomative [4+2] Cyclodimerization of In-situ Generated ortho-Quinone Methides
Sahoo, Sushree Ranjan
Singh, Vinod K.
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 12 (11)
[7] Asymmetric Bronsted Acid Catalyzed Cycloadditions of ortho-Quinone Methides and Related Compounds
Dorsch, Caroline
Schneider, Christoph
SYNTHESIS-STUTTGART, 2022, 54 (14): : 3125 - 3141
[8] Facile Synthesis of Spirocyclic Oxindole Scaffolds via Intermolecular [4+1] Cycloaddition of ortho-Quinone Methides with 3-Chlorooxindoles
Wang, Mao-Chang
Wei, Peng
Li, Peiwu
Lin, Chao
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2024, 56 (04) : 350 - 370
[9] Enantioselective Addition of Thiols to ortho-Quinone Methides Catalyzed by Chiral Phosphoric Acids
Lai, Zengwei
Sun, Jianwei
SYNLETT, 2016, 27 (04) : 555 - 558
[10] Phosphoric Acid Catalyzed [4+1]-Cycloannulation Reaction of ortho-Quinone Methides and Diazoketones: Catalytic, Enantioselective Access toward cis-2,3-Dihydrobenzofurans
Suneja, Arun
Schneider, Christoph
ORGANIC LETTERS, 2018, 20 (23) : 7576 - 7580

← 1 2 3 4 5 →