Ynol Ethers: Synthesis and Reactivity

被引：4

作者：

Verrier, Charlie ^{[1
]}

Carret, Sebastien ^{[1
]}

Poisson, Jean-Francois ^{[1
]}

机构：

[1] Univ Grenoble Alpes, Dept Chim Mol SERCO, UMR 5250, CNRS,IMCG FR 2607, F-38041 Grenoble, France

来源：

CHIMIA | 2016年 / 70卷 / 1-2期

关键词：

Alkynes; Enol ethers; Ketenes; Synthesis; Ynol ethers; ACETYLENIC ETHERS; ALKYNYL ETHERS; INTRAMOLECULAR CARBOLITHIATION; ASYMMETRIC-SYNTHESIS; EFFICIENT SYNTHESIS; 2+2 CYCLOADDITION; CHEMISTRY; CARBANIONS; REAGENTS; STRATEGY;

D O I：

10.2533/chimia.2016.93

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Ynol ethers are highly valuable substrates offering a wide range of reactivity. These highly electron rich heterosubstitued alkynes can be of great synthetic potential. In this mini-review, the different methods for the synthesis of ynol ethers are first presented, divided in three main approaches involving a beta-elimination, a carbene rearrangement and a direct oxidation of an alkyne. Their reactivity is then summarized underlying their synthetic utility. This non-exhaustive review aims at presenting the intrinsic reactivity of these compounds, still underexploited in synthesis.

引用

页码：93 / 96

页数：4

共 50 条

[31] SYNTHESIS AND REACTIVITY OF ALLENYLVINYL CYCLOALK-2-ENYL ETHERS
DULCERE, JP
AGATI, V
RODRIGUEZ, J
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (12) : 1038 - 1039
[32] Gold-Catalyzed Regio- and Stereoselective α-Acyloxy-β-Alkynylation of Ynol Ethers
Liu, Yaowen
Han, Chunyu
Shi, Hongwei
V. Mackenroth, Alexandra
Zhang, Linghua
Rudolph, Matthias
Rominger, Frank
Hashmi, A. Stephen K.
JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (05): : 2908 - 2920
[33] REACTIVITY OF CYCLOPROPANE ETHERS
GALY, JP
COMPTES RENDUS HEBDOMADAIRES DES SEANCES DE L ACADEMIE DES SCIENCES SERIE C, 1972, 275 (25): : 1531 - 1533
[34] Copper-Catalyzed Coupling of 1,1-Dibromo-1-alkenes with Phenols: A General, Modular, and Efficient Synthesis of Ynol Ethers, Bromo Enol Ethers, and Ketene Acetals
Jouvin, Kevin
Bayle, Alexandre
Legrand, Frederic
Evano, Gwilherm
ORGANIC LETTERS, 2012, 14 (06) : 1652 - 1655
[35] Silver-Catalyzed Regio- and Stereoselective Addition of Carboxylic Acids to Ynol Ethers
Yin, Jing
Bai, Yihui
Mao, Mengyi
Zhu, Gangguo
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (19): : 9179 - 9185
[36] Palladium-Catalyzed Hydroarylation, Hydroalkenylation, and Hydrobenzylation of Ynol Ethers with Organohalides: A Regio- and Stereoselective Entry to α,β- and β,β-Disubstituted Alkenyl Ethers
Cui, Weijian
Yin, Jing
Zheng, Renwei
Cheng, Cungui
Bai, Yihui
Zhu, Gangguo
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (08): : 3487 - 3493
[37] Extending the utility of ynol ethers for carbon-carbon bond formation: Synthesis of α-alkylidene-, α-benzylidene-, α-methylene-γ-butyrolactones, and δ-valerolactones
Minehan, Thomas
Ng, Kevin
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 251
[38] Aryl Ynol Ethers: Stable, Readily Available and Useful Precursors of Highly Reactive Ketenium Ions
Lecomte, Morgan
Evano, Gwilherm
LETTERS IN ORGANIC CHEMISTRY, 2017, 14 (08) : 539 - 542
[39] Site-specific introduction of gold-carbenoids by intermolecular oxidation of ynamides or ynol ethers
Davies, Paul W.
Cremonesi, Alex
Martin, Nicolas
CHEMICAL COMMUNICATIONS, 2011, 47 (01) : 379 - 381
[40] YNOL SILYL ETHERS VIA O-SILYLATION OF ESTER-DERIVED YNOLATE ANIONS
KOWALSKI, CJ
LAL, GS
HAQUE, MS
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (22) : 7127 - 7128

← 1 2 3 4 5 →