An efficient stereoselective synthesis of functionalized vinyl ethers

被引：2

作者：

Balalaie, Saeed ^{[1
]}

Kassaee, Mohammad Z. ^{[2
]}

Bijanzadeh, Hamid Reza ^{[1
]}

Darvish, Fatemeh ^{[1
]}

Bararjanian, Morteza ^{[1
]}

Jalaiyan, Fatemeh ^{[1
]}

机构：

[1] KN Toosi Univ Technol, Peptide Chem Res Ctr, Tehran, Iran

[2] Tarbiat Modares Univ, Dept Chem, Tehran, Iran

来源：

JOURNAL OF THE IRANIAN CHEMICAL SOCIETY | 2014年 / 11卷 / 05期

基金：

美国国家科学基金会;

关键词：

Functionalized vinyl ethers; Nucleophilic addition to active alkynes; Ugi-4CR; Ugi-4CR post-transformation; N-substituted; 2-alkynamides; SUBSTITUTION; ALCOHOLS; ESTERS;

D O I：

10.1007/s13738-014-0418-6

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient regio and stereoselective synthesis of functionalized E-vinyl ethers are described. The reaction could proceed via addition of primary alcohols and phenols to functionalized N-substituted 2-alkynamides which are produced via Ugi-4CR in the presence of triethylamine at room temperature. The reaction proceeds through sequential Ugi/nucleophilic reaction sequence. High yields, short reaction times, and simple operations are the advantages of this approach.

引用

页码：1483 / 1492

页数：10

共 50 条

[31] Use of Iridium-Catalyzed Transfer Vinylation for the Synthesis of Bio-Based (bis)-Vinyl Ethers [J].

Spiegelberg, Brian ;

Jiao, Haijun ;

Grauke, Reni ;

Kubis, Christoph ;

Spannenberg, Anke ;

Brandt, Adrian ;

Taden, Andreas ;

Beck, Horst ;

Tin, Sergey ;

Vries, Johannes G. .

ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (07) :1251-1263

[32] Palladium-Catalyzed Dimerization of Vinyl Ethers to Acetals [J].

Chen, Changle ;

Jordan, Richard F. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (30) :10254-10255

[33] Convenient and efficient synthesis of functionalized unsymmetrical Z-alkenyl disulfanes [J].

Musiejuk, M. ;

Doroszuk, J. ;

Witt, D. .

RSC ADVANCES, 2018, 8 (18) :9718-9722

[34] Vinyl ethers and epoxides photoinduced copolymerization with perfluoropolyalkylether monomers [J].

Trusiano, Giuseppe ;

Vitale, Alessandra ;

Bonneaud, Celine ;

Pugliese, Diego ;

Dalle Vacche, Sara ;

Joly-Duhamel, Christine ;

Friesen, Chadron M. ;

Bongiovanni, Roberta .

COLLOID AND POLYMER SCIENCE, 2021, 299 (03) :509-521

[35] Nucleophilic Heterocyclic Carbene Catalyzed Annulation of Enals to Chalcones in Methanol: A Stereoselective Synthesis of Highly Functionalized Cyclopentanes [J].

Nair, Vijay ;

Babu, Beneesh P. ;

Vellalath, Sreekumar ;

Varghese, Vimal ;

Raveendran, Anabha E. ;

Suresh, Eringathodi .

ORGANIC LETTERS, 2009, 11 (12) :2507-2510

[36] Stereoselective Synthesis of Functionalized Pyrrolidines by the Diverted N-H Insertion Reaction of Metallocarbenes with -Aminoketone Derivatives [J].

Nicolle, Simon M. ;

Lewis, William ;

Hayes, Christopher J. ;

Moody, Christopher J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (11) :3749-3753

[37] Synthesis of functionalized α-trifluoroethyl amine scaffolds via Grignard addition to N-aryl hemiaminal ethers [J].

Deutsch, Amrei ;

Glas, Herbert ;

Hoffmann-Roeder, Anja ;

Deutsch, Carl .

RSC ADVANCES, 2014, 4 (18) :9288-9291

[38] An Efficient Stereoselective Approach for the Synthesis of (+)-( 4S,5S)-Muricatacin [J].

Srinivas, Chiguru ;

Kumar, Chebolu Naga Sesha Sai Pavan ;

Raju, Bhimapaka China ;

Rao, Vaidya Jayathirtha .

HELVETICA CHIMICA ACTA, 2011, 94 (04) :669-674

[39] Gold(I)-catalyzed Claisen rearrangement of allenyl vinyl ethers; synthesis of substituted 1,3-dienes [J].

Krafft, Marie E. ;

Hallal, Kassem M. ;

Vidhani, Dinesh V. ;

Cran, John W. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (21) :7535-7538

[40] Stereoselective Synthesis of Dysoxylactam A [J].

Chandankar, Somnath S. ;

Raghavan, Sadagopan .

ORGANIC LETTERS, 2020, 22 (02) :653-655

← 1 2 3 4 5 →