Synthesis of SF5-substituted isoxazolidines using 1,3-dipolar cycloaddition reactions of nitrones with pentafluorosulfanyl acrylic esters and amides

被引:22
作者
Falkowska, Ewelina [1 ,2 ]
Laurent, Mathieu Y. [3 ]
Tognetti, Vincent [1 ,2 ]
Joubert, Laurent [1 ,2 ]
Jubault, Philippe [1 ,2 ]
Bouillon, Jean-Philippe [1 ,2 ]
Pannecoucke, Xavier [1 ,2 ]
机构
[1] Normandie Univ, COBRA, UMR 6014, F-76821 Mont St Aignan, France
[2] Univ Rouen, FR 3038, INSA Rouen, CNRS, F-76821 Mont St Aignan, France
[3] LUNAM Univ Maine, Inst Mol & Mat Mans, UMR CNRS 6283, F-72085 Le Mans 9, France
关键词
Fluorine; Pentafluorosulfanyl; 1,3-Dipolar cycloaddition; Heterocycle; Isoxazolidine; DUAL DESCRIPTOR; FLUORINE; TRIFLUOROMETHYLATION; CHEMISTRY; ALKENES; ACCESS;
D O I
10.1016/j.tet.2015.08.050
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
1,3-Dipolar cycloadditions of nitrones with pentafluorosulfanyl-substituted acrylic ester and amides afforded new trisubstituted pentafluorosulfanylated isoxazolidines in moderate yields as 4-SF5-regioisomers. Theoretical calculations were carried out and the regioselectivity could be explained by the fact that the 5-SF5-regioisomer probably undertook a spontaneous degradation in the reaction medium via the loss of pentafluorosulfanyl anion. Diastereoselectivity of the 1,3-dipolar cycloadditions was also assessed according to NMR and X-ray diffraction analysis. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码:8067 / 8076
页数:10
相关论文
共 62 条
[1]   Electrophilic Trifluoromethylthiolation of Carbonyl Compounds [J].
Alazet, Sebastien ;
Zimmer, Luc ;
Billard, Thierry .
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (28) :8589-8593
[2]   Synthetic chemistry and biological activity of pentafluorosulphanyl (SF5) organic molecules [J].
Altomonte, Stefano ;
Zanda, Matteo .
JOURNAL OF FLUORINE CHEMISTRY, 2012, 143 :57-93
[3]   ATOMS IN MOLECULES [J].
BADER, RFW .
ACCOUNTS OF CHEMICAL RESEARCH, 1985, 18 (01) :9-15
[4]  
Bgu J.-P., 2008, Bioorganic and Medicinal Chemistry of Fluorine, DOI 10.1002/9780470281895
[5]   Recent Progress in Asymmetric Fluorination and Trifluoromethylation Reactions [J].
Bizet, Vincent ;
Besset, Tatiana ;
Ma, Jun-An ;
Cahard, Dominique .
CURRENT TOPICS IN MEDICINAL CHEMISTRY, 2014, 14 (07) :901-940
[6]   A CYCLOADDITIVE ROUTE TO TRIFLUOROMETHYL-SUBSTITUTED AMINOALCOHOLS [J].
BRAVO, P ;
BRUCHE, L ;
FRONZA, G ;
ZECCHI, G .
TETRAHEDRON, 1992, 48 (44) :9775-9788
[7]  
Bravo P., 1991, J CHEM RES, V81, P719
[8]   Long-range corrected hybrid density functionals with damped atom-atom dispersion corrections [J].
Chai, Jeng-Da ;
Head-Gordon, Martin .
PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2008, 10 (44) :6615-6620
[9]   Structure-Guided Lead Optimization of Triazolopyrimidine-Ring Substituents Identifies Potent Plasmodium falciparum Dihydroorotate Dehydrogenase Inhibitors with Clinical Candidate Potential [J].
Coteron, Jose M. ;
Marco, Maria ;
Esquivias, Jorge ;
Deng, Xiaoyi ;
White, Karen L. ;
White, John ;
Koltun, Maria ;
El Mazouni, Farah ;
Kokkonda, Sreekanth ;
Katneni, Kasiram ;
Bhamidipati, Ravi ;
Shackleford, David M. ;
Angulo-Barturen, Inigo ;
Ferrer, Santiago B. ;
Belen Jimenez-Diaz, Maria ;
Gamo, Francisco-Javier ;
Goldsmith, Elizabeth J. ;
Charman, William N. ;
Bathurst, Ian ;
Floyd, David ;
Matthews, David ;
Burrows, Jeremy N. ;
Rathod, Pradipsinh K. ;
Charman, Susan A. ;
Phillips, Margaret A. .
JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (15) :5540-5561
[10]   Preparation of Pentafluorosulfanyl (SF5) Pyrrole Carboxylic Acid Esters [J].
Dolbier, William R., Jr. ;
Zheng, Zhaoyun .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (15) :5626-5628