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

[31] Enantioselective Formal [4+2] Annulation of ortho-Quinone Methides with ortho-Hydroxyphenyl α,β-Unsaturated Compounds
Zhang, Jianlin
Liu, Xiaohua
Guo, Songsong
He, Changqiang
Xiao, Wanlong
Lin, Lili
Feng, Xiaoming
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (17): : 10175 - 10185
[32] Catalytic Asymmetric Intramolecular [4+2] Cycloaddition of In Situ Generated ortho-Quinone Methides
Xie, Youwei
List, Benjamin
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (18) : 4936 - 4940
[33] Organocatalytic Asymmetric [2+4] Cycloadditions of 3-Vinylindoles with ortho-Quinone Methides
Liu, Si-Jia
Tu, Man-Su
Liu, Kai-Yue
Chen, Jia-Yi
Ni, Shao-Fei
Zhang, Yu-Chen
Shi, Feng
MOLECULES, 2021, 26 (21):
[34] Asymmetric isochalcogenourea-catalysed (4+2)-cycloadditions of ortho-quinone methides and allenoates
Scheucher, Anna
Gross, Christoph
Piringer, Magdalena
Novacek, Johanna
Ofial, Armin R.
Waser, Mario
ORGANIC & BIOMOLECULAR CHEMISTRY, 2025, 23 (04) : 827 - 834
[35] Catalytic Asymmetric [4+3] Cyclizations of 2-Indolylmethanols with ortho-Quinone Methides
Liu, Lu
Zhang, Junliang
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2019, 39 (11) : 3308 - 3309
[36] Dearomatization of Halonaphthols via an Intermolecular [4+1] Spiroannulation with in situ Formed Aza-ortho-quinone Methides
Liang, Junxiu
Liu, Yazhou
Wang, Amu
Wu, Yanchao
Ma, Xiaofeng
Li, Huijing
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2023, 43 (11) : 3888 - 3899
[37] A [4+1] annulation of ortho-electrophile-substituted para-quinone methides for the synthesis of indanes and isoindolines
Feng, Ziwen
Yuan, Zhenbo
Zhao, Xiaobin
Huang, Yue
Yao, Hequan
ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (20) : 3535 - 3539
[38] Chiral phosphoric acid catalyzed enantioselective annulation of acyclic enecarbamates to in situ-generated ortho-quinone methides
Gharui, Chandan
Singh, Shreya
Pan, Subhas Chandra
ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (35) : 7272 - 7276
[39] Base-Catalyzed Decarboxylative Amination of In-Situ Generated Ortho-Quinone Methides: Synthesis of Benzyl Amines
Sahoo, Sushree Ranjan
Subba, Parbat
Singh, Vinod K.
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 13 (10)
[40] Base-mediated diastereoselective [4+3] annulation of in situ generated ortho-quinone methides with C, N-cyclic azomethine imines
Xu, Jianfeng
Yuan, Shiru
Peng, Jingyi
Miao, Maozhong
Chen, Zhengkai
Ren, Hongjun
ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (36) : 7513 - 7517

← 1 2 3 4 5 →