On the formation of seven-membered rings by arene-ynamide cyclization

被引:12
作者
Brutiu, Bogdan R. [1 ]
Bubeneck, Wilhelm Andrei [1 ]
Cvetkovic, Olivera [1 ]
Li, Jing [1 ]
Maulide, Nuno [1 ]
机构
[1] Univ Vienna, Inst Organ Chem, Wahringer Str 38, A-1090 Vienna, Austria
来源
MONATSHEFTE FUR CHEMIE | 2019年 / 150卷 / 01期
基金
奥地利科学基金会;
关键词
Heterocycles; Strained molecules; BrOnsted acid; Catalysis; SULFONIUM; ACCESS;
D O I
10.1007/s00706-018-2320-x
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A BrOnsted acid-catalyzed selective arene-ynamide cyclization is described. This reaction proceeds via a keteniminium intermediate and enables the preparation of seven-membered ring enamide products. Mechanistic studies uncover an unusual product inhibition behavior. [GRAPHICS] .
引用
收藏
页码:3 / 10
页数:8
相关论文
共 26 条
[1]   Ynamide Preactivation Allows a Regio- and Stereoselective Synthesis of α,β-Disubstituted Enamides [J].
Baldassari, Lucas L. ;
de la Torre, Aurelien ;
Li, Jing ;
Luedtke, Diogo S. ;
Maulide, Nuno .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (49) :15723-15727
[2]   Ynamides: A Modern Functional Group for the New Millennium [J].
DeKorver, Kyle A. ;
Li, Hongyan ;
Lohse, Andrew G. ;
Hayashi, Ryuji ;
Lu, Zhenjie ;
Zhang, Yu ;
Hsung, Richard P. .
CHEMICAL REVIEWS, 2010, 110 (09) :5064-5106
[3]   A Journey in the Chemistry of Ynamides: From Synthesis to Applications [J].
Evano, Gwilherm ;
Blanchard, Nicolas ;
Compain, Guillaume ;
Coste, Alexis ;
Demmer, Charles S. ;
Gati, Wafa ;
Guissart, Celine ;
Heimburger, Jeremy ;
Henry, Nicolas ;
Jouvin, Kevin ;
Karthikeyan, Ganesan ;
Laouiti, Anouar ;
Lecomte, Morgan ;
Martin-Mingot, Agnes ;
Metayer, Benoit ;
Michelet, Bastien ;
Nitelet, Antoine ;
Theunissen, Cedric ;
Thibaudeau, Sebastien ;
Wang, Jianjun ;
Zarca, Maxence ;
Zhang, Chunyang .
CHEMISTRY LETTERS, 2016, 45 (06) :574-585
[4]  
Evano G, 2015, ALDRICHIM ACTA, V48, P59
[5]   General Amination Reactions for the Synthesis of Ynamides [J].
Evano, Gwilherm ;
Jouvin, Kevin ;
Coste, Alexis .
SYNTHESIS-STUTTGART, 2013, 45 (01) :17-26
[6]   NMR chemical shifts of common laboratory solvents as trace impurities [J].
Gottlieb, HE ;
Kotlyar, V ;
Nudelman, A .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (21) :7512-7515
[7]   Isolation and First Total Synthesis of PM050489 and PM060184, Two New Marine Anticancer Compounds [J].
Jesus Martin, Maria ;
Coello, Laura ;
Fernandez, Rogelio ;
Reyes, Fernando ;
Rodriguez, Alberto ;
Murcia, Carmen ;
Garranzo, Maria ;
Mateo, Cristina ;
Sanchez-Sancho, Francisco ;
Bueno, Santiago ;
de Eguilior, Carlos ;
Francesch, Andres ;
Munt, Simon ;
Cuevas, Carmen .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (27) :10164-10171
[8]   Stereodivergent synthesis of 1,4-dicarbonyls by traceless charge-accelerated sulfonium rearrangement [J].
Kaldre, Dainis ;
Klose, Immo ;
Maulide, Nuno .
SCIENCE, 2018, 361 (6403) :664-667
[9]   An Asymmetric Redox Arylation: Chirality Transfer from Sulfur to Carbon through a Sulfonium [3,3]-Sigmatropic Rearrangement [J].
Kaldre, Dainis ;
Maryasin, Boris ;
Kaiser, Daniel ;
Gajsek, Oliver ;
Gonzalez, Leticia ;
Maulide, Nuno .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (08) :2212-2215
[10]   Harnessing the Electrophilicity of Keteniminium Ions: A Simple and Straightforward Entry to Tetrahydropyridines and Piperidines from Ynamides [J].
Lecomte, Morgan ;
Evano, Gwilherm .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (14) :4547-4551