A convenient synthesis of N-vinyl enamides via the lithiation and ring-opening reaction of 2-phenyl-2-oxazolines

被引:5
作者
Xu, Yi [1 ]
Liu, Xiao-Yu [1 ]
Wang, Zi-Qi [1 ]
Tang, Liang-Fu [1 ]
机构
[1] Nankai Univ, Dept Chem, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China
基金
中国国家自然科学基金;
关键词
Oxazoline; Enamide; Lithiation; Ring-opening reaction; VERSATILE BUILDING-BLOCKS; STEREOSELECTIVE-SYNTHESIS; TERTIARY ENAMIDES; ASYMMETRIC-SYNTHESIS; DERIVATIVES; YNAMIDES; ISOMERIZATION; ALLYLAMIDES; AMIDES; REGIO;
D O I
10.1016/j.tetlet.2017.03.080
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple and efficient synthesis of N-vinyl enamides via the lithiation and ring-opening reaction of 2-phenyl-2-oxazolines with lithium diisopropylamide at room temperature has been developed. This method is especially suitable for the synthesis of multifunctional enamides. Good yields have been obtained when the reactions were amplified to gram scale. (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1788 / 1791
页数:4
相关论文
共 48 条
[1]   Synthesis of marine brominated alkaloid amathamide F: a palladium-catalyzed enamide synthesis [J].
Ahmad, Saeed ;
Choudhury, Sumit ;
Khan, Faiz Ahmed .
TETRAHEDRON, 2015, 71 (24) :4192-4202
[2]   Enamide Derivatives: Versatile Building Blocks for Highly Functionalized α,β-Substituted Amines [J].
Bernadat, Guillaume ;
Masson, Geraldine .
SYNLETT, 2014, 25 (20) :2842-2867
[3]   Copper-catalyzed cross-coupling of amides and potassium alkenyltrifluoroborate salts: a general approach to the synthesis of enamides [J].
Bolshan, Yuri ;
Batey, Robert A. .
TETRAHEDRON, 2010, 66 (27-28) :5283-5294
[4]   Enamides: valuable organic substrates [J].
Carbery, David R. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (19) :3455-3460
[5]  
Carey F. A., 2000, ADV ORGANIC CHEM A, P237
[6]   n-Butyllithium/N,N,N',N'-tetramethylethylenediamine-mediated ortholithiations of aryl oxazolines:: Substrate-dependent mechanisms [J].
Chadwick, Scott T. ;
Ramirez, Antonio ;
Gupta, Lekha ;
Collum, David B. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (08) :2259-2268
[7]   Enamide Derivatives: Versatile Building Blocks for Total Synthesis [J].
Courant, Thibaut ;
Dagousset, Guillaume ;
Masson, Geraldine .
SYNTHESIS-STUTTGART, 2015, 47 (13) :1799-1826
[8]   COMPARATIVE-STUDY OF THE PHOTOREACTIVITY OF TERTIARY AROMATIC ENAMIDES AND THIOENAMIDES [J].
COUTURE, A ;
DUBIEZ, R ;
LABLACHECOMBIER, A .
TETRAHEDRON, 1984, 40 (10) :1835-1844
[9]   Synthesis of enamines, enol ethers and related compounds by cross-coupling reactions [J].
Dehli, JR ;
Legros, J ;
Bolm, C .
CHEMICAL COMMUNICATIONS, 2005, (08) :973-986
[10]   Synthesis of Tertiary Enamides by Ag2CO3-Promoted Pd-Catalyzed Alkenylation of Acyclic Secondary Amides [J].
Delforge, Arnaud ;
Georgiou, Irene ;
Kremer, Adrian ;
Wouters, Johan ;
Bonifazi, Davide .
ORGANIC LETTERS, 2016, 18 (19) :4844-4847