Preparation of vinyl ethers using a Wittig approach, and their subsequent hydrogenation employing continuous-flow processing

被引:12
作者
Balti, Monaem [1 ]
Efrit, Mohamed Lotfi [1 ]
Leadbeater, Nicholas E. [2 ]
机构
[1] Univ El Manar, Lab Organ Synth & Heterocycl Chem, Fac Sci Tunis, Dept Chem, Tunis, Tunisia
[2] Univ Connecticut, Dept Chem, 55 North Eagleville Rd, Storrs, CT 06269 USA
关键词
Wittig reaction; Vinyl ether; Enol ethers; Hydrogenation; Flow chemistry; NAZAROV CYCLIZATION; ALCOHOLS; OLEFINATION; LACTONES; CATALYST; ACCESS; CORE;
D O I
10.1016/j.tetlet.2016.03.037
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A methodology is reported for the preparation of various aromatic-functionalized vinyl ethers using a Wittig approach. The subsequent hydrogenation of the vinyl ether products to their saturated analogs is also performed and is streamlined by employing continuous-flow processing. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1804 / 1806
页数:3
相关论文
共 41 条
[1]   A Renaissance in Living Cationic Polymerization [J].
Aoshima, Sadahito ;
Kanaoka, Shokyoku .
CHEMICAL REVIEWS, 2009, 109 (11) :5245-5287
[2]   The integration of flow reactors into synthetic organic chemistry [J].
Baxendale, Ian R. .
JOURNAL OF CHEMICAL TECHNOLOGY AND BIOTECHNOLOGY, 2013, 88 (04) :519-552
[3]   Total synthesis of the rubrolone aglycon [J].
Boger, DL ;
Ichikawa, S ;
Jiang, HJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (49) :12169-12173
[4]   Synthesis of 1-phenyl- and 1-pyridyl-3-pyridoazepines by reductive cyclization of diarylacetonitriles [J].
Carmen de la Fuente, M. ;
Dominguez, Domingo .
TETRAHEDRON, 2009, 65 (18) :3653-3658
[5]   Silica-Immobilized Chiral Dirhodium(II) Catalyst for Enantioselective Carbenoid Reactions [J].
Chepiga, Kathryn M. ;
Feng, Yan ;
Brunelli, Nicholas A. ;
Jones, Christopher W. ;
Davies, Huw M. L. .
ORGANIC LETTERS, 2013, 15 (24) :6136-6139
[6]   Discovery of a potent, metabolically stabilized resorcylic lactone as an anti-inflammatory lead [J].
Du, H. ;
Matsushima, T. ;
Spyvee, M. ;
Goto, M. ;
Shirota, H. ;
Gusovsky, F. ;
Chiba, K. ;
Kotake, M. ;
Yoneda, N. ;
Eguchi, Y. ;
DiPietro, L. ;
Harmange, J. -C. ;
Gilbert, S. ;
Li, X. -Y. ;
Davis, H. ;
Jiang, Y. ;
Zhang, Z. ;
Pelletier, R. ;
Wong, N. ;
Sakurai, H. ;
Yang, H. ;
Ito-Igarashi, H. ;
Kimura, A. ;
Kuboi, Y. ;
Mizui, Y. ;
Tanaka, I. ;
Ikemori-Kawada, M. ;
Kawakami, Y. ;
Inoue, A. ;
Kawai, T. ;
Kishi, Y. ;
Wang, Y. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (21) :6196-6199
[7]   SYNTHESIS OF E-VINYL AND Z-VINYL ETHERS BY THE HORNER-WITTIG REACTION [J].
EARNSHAW, C ;
WALLIS, CJ ;
WARREN, S .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (12) :3099-3106
[8]  
Edmonds M., 2003, MODERN CARBONYL OLEF, P1
[9]   Continuous-Flow TechnologyA Tool for the Safe Manufacturing of Active Pharmaceutical Ingredients [J].
Gutmann, Bernhard ;
Cantillo, David ;
Kappe, C. Oliver .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (23) :6688-6728
[10]   Polarizing the Nazarov cyclization: The impact of dienone substitution pattern on reactivity and selectivity [J].
He, Wei ;
Herrick, Ildiko R. ;
Atesin, Tulay A. ;
Caruana, Patrick A. ;
Kellenberger, Colleen A. ;
Frontier, Alison J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (03) :1003-1011