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

[21] Recent advances in [4+4] annulation of conjugated heterodienes with 1,4-dipolar species for the synthesis of eight-membered heterocycles
Wang, Yahui
Jin, Zefeng
Zhou, Liejin
Lv, Xin
ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (02) : 252 - 268
[22] Recent advances in the therapeutic application of short-chain fatty acids (SCFAs): An updated review
Rauf, Abdur
Khalil, Anees Ahmed
Rahman, Ubaid-Ur
Khalid, Ahood
Naz, Saima
Shariati, Mohammad Ali
Rebezov, Maksim
Urtecho, Ewaldo Zavala
de Albuquerque, Ricardo Diego Duarte Galhardo
Anwar, Sirajudheen
Alamri, Abdulwahab
Saini, Ramesh Kumar
Rengasamy, Kannan R. R.
CRITICAL REVIEWS IN FOOD SCIENCE AND NUTRITION, 2022, 62 (22) : 6034 - 6054
[23] Highly Diastereoselective Synthesis of 2,3-Dihydropyrroles via Formal [4+1] Annulation Reaction of α,β-Unsaturated Imines and in Situ Generated Pyridinium Ylide
Saha, Suman K.
Bera, Anupriya
Kumari, Akanksha
Shukla, Khyati
Rana, Nirmal K.
JOURNAL OF ORGANIC CHEMISTRY, 2024, 90 (01): : 853 - 862
[24] Proline-Catalyzed Sequential syn-Mannich and [4+1]-Annulation Cascade Reactions To Form Densely Functionalized Pyrrolidines
Aher, Ravindra D.
Kumar, B. Senthil
Sudalai, Arumugam
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (03): : 2024 - 2031
[25] RECENT ADVANCES IN THE APPLICATION OF OXADIAZOLES IN MULTICOMPONENT REACTIONS FROM 2015-16: A REVIEW
Somashekhar, M.
Kotnal, R. B.
INDO AMERICAN JOURNAL OF PHARMACEUTICAL SCIENCES, 2018, 5 (08): : 7632 - 7644
[26] Gold-Catalyzed [4+1]-Annulation Reactions between 1,4-Diyn-3-ols and Isoxazoles To Construct a Pyrrole Core
Kardile, Rahul Dadabhau
Kale, Balaji S.
Sharma, Pankaj
Liu, Rai-Shung
ORGANIC LETTERS, 2018, 20 (13) : 3806 - 3809
[27] Phosphine vs DBU-Catalyzed Annulation Reactions of β′-Acetoxy Allenoates with Acyl-Tethered Benzothiazole Bisnucleophiles: (4+3) or (4+1) vs (3+3) Annulation
Chauhan, Sachin
Swamy, K. C. Kumara
JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (15): : 10816 - 10830
[28] Metal free [4+1] and [5+1] annulation reactions to prepare heterocycles using DMF and its derivatives as one-carbon source
Xu, Yiwen
Shen, Bei
Liu, Lingfeng
Qiao, Chunhua
TETRAHEDRON LETTERS, 2020, 61 (19)
[29] Rh(<sc>iii</sc>)-catalyzed [4+1] annulation of a sulfoxonium ylide with allyl alkyl ethers: a detailed theoretical study of the anti-inflammatory and antidiabetic activities with DFT
Sivakumar, Pakkirisamy
Ganesh, Pothapragada S. K. Prabhakar
Muthuraja, Perumal
Bharanidharan, Sarangapani
Anandhan, Balasubramaniyan
Rajamohan, Rajaram
Kamatchi, Subramaniyan
NEW JOURNAL OF CHEMISTRY, 2024, 48 (36) : 15989 - 15999
[30] Recent advance in transition-metal-catalyzed oxidant-free 4+1 annulation through C-H bond activation
Zhu, Chuan
Wang, Cheng-Qiang
Feng, Chao
TETRAHEDRON LETTERS, 2018, 59 (05) : 430 - 437

← 1 2 3 4 5 →