Recent advances in the application of ylide-like species in [4+1]-annulation reactions: an updated review

被引：31

作者：

Ushakov, Pavel Yu ^{[1
]}

Loffe, Sema L. ^{[1
]}

Sukhorukov, Alexey Yu ^{[1
]}

机构：

[1] ND Zelinskii Inst Organ Chem, Lab Organ & Met Organ Nitrogen Oxygen Syst, Leninsky Prospect 47, Moscow 119991, Russia

来源：

ORGANIC CHEMISTRY FRONTIERS | 2022年 / 9卷 / 19期

基金：

俄罗斯科学基金会;

关键词：

FORMAL 4+1 ANNULATION; CATALYZED DIASTEREOSELECTIVE SYNTHESIS; PARA-QUINONE METHIDES; SULFUR YLIDES; ENANTIOSELECTIVE SYNTHESIS; FACILE SYNTHESIS; ASYMMETRIC-SYNTHESIS; ALPHA-ARYLHYDRAZONOKETONES; AMMONIUM YLIDES; ARSONIUM YLIDES;

D O I：

10.1039/d2qo00698g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this review, the advances made over the last 6 years in [4 + 1]-annulation reactions involving sulfonium, sulfoxonium and ammonium ylides, as well as diazo compounds and carbenes are summarized. The newly emerged methods for generating A(4)-synthons, such as radical, transition metal-catalyzed and photo-redox processes, are outlined. A specific focus is given on the progress in asymmetric [4 + 1]-annulations using organocatalysis and chiral ammonium ylides.

引用

页码：5358 / 5382

页数：25

共 48 条

[1] Recent Advances in Phosphine-Promoted (4+1) Annulation Reactions
Zhang, Heng
Zhou, Rong
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (27) : 4098 - 4107
[2] Ylide formal [4+1] annulation
Zhu, Chunyin
Ding, Ya
Ye, Long-Wu
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (09) : 2530 - 2536
[3] Diastereoselective synthesis of trans-2,3-dihydroindoles via formal [4+1] annulation reactions of a sulfonium ylide
Jain, Anshul
Kumari, Akanksha
Metre, Ramesh K.
Rana, Nirmal K.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (03) : 621 - 632
[4] Sulfur Ylide Initiated [4+1]/[4+2] Annulation Reactions: A One-Pot Approach to Dibenzofuran Acrylate Derivatives
Shao, Jiaan
Chen, Wenteng
Ying, Zhimin
Liu, Shuangrong
Luo, Feng
Ou, Lili
ORGANIC LETTERS, 2019, 21 (16) : 6370 - 6373
[5] Sulfoxonium-Ylide-Directed C-H Activation and Tandem (4+1) Annulation
Hanchate, Vinayak
Devarajappa, Ravi
Prabhu, Kandikere Ramaiah
ORGANIC LETTERS, 2020, 22 (08) : 2878 - 2882
[6] Highly diastereoselective and enantioselective formal [4+1] ylide annulation for the synthesis of optically active dihydrofurans
Zheng, Jun-Cheng
Zhu, Chun-Yin
Sun, Xiu-Li
Tang, Yong
Dai, Li-Xin
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (17): : 6909 - 6912
[7] Asymmetric Sulfur-Ylide-Mediated Formal [4+1]-Annulation Reaction: Scope and Mechanism
Clergue, Sebastien
Rousseau, Olivier
Delaunay, Thierry
Dequirez, Geoffroy
Trieu-Van Tran
El Aakchioui, Soumia
Barozzino-Consiglio, Gabriella
Robiette, Raphael
CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (44) : 11417 - 11425
[8] Formal [4+1] Annulation Reactions in the Synthesis of Carbocyclic and Heterocyclic Systems
Chen, Jia-Rong
Hu, Xiao-Qiang
Lu, Liang-Qiu
Xiao, Wen-Jing
CHEMICAL REVIEWS, 2015, 115 (11) : 5301 - 5365
[9] Diastereoselective and Enantioselective Formal [4+1] Ylide Annulation Leading to Optically Active Isoxazoline N-Oxides
Gong, Pin
Wang, Jing
Yao, Wen-Bo
Xie, Xuan-Sheng
Xie, Jian-Wu
ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (06) : 1185 - 1199
[10] Synthesis of Heterocyclic-Fused Furans and Dihydrofurans via (4+1)-Annulation with Ylide: Exploration of Unique Reactivity Behavior of α-Carbonyl Sulfoxonium Ylide
Kumar, Gulshan
Nagpure, Mithilesh
Rao, Vajja Krishna
Guchhait, Sankar K.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (16)

← 1 2 3 4 5 →