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

来源：

TETRAHEDRON | 2015年 / 71卷 / 42期

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

页码：8067 / 8076

页数：10

共 62 条

[11] Trifluoromethylation of Alkenes with Concomitant Introduction of Additional Functional Groups [J].

Egami, Hiromichi ;

Sodeoka, Mikiko .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (32) :8294-8308

[12] Understanding the regioselectivity and molecular mechanism in the synthesis of isoxazoles containing pentafluorosulfanyl substitution via a [3+2] cycloaddition reaction: A DFT study [J].

Emamian, Saeedreza .

JOURNAL OF FLUORINE CHEMISTRY, 2015, 178 :165-172

[13] First efficient synthesis of SF5-substituted pyrrolidines using 1,3-dipolar cycloaddition of azomethine ylides with pentafluorosulfanyl-substituted acrylic esters and amides [J].

Falkowska, Ewelina ;

Tognetti, Vincent ;

Joubert, Laurent ;

Jubault, Philippe ;

Bouillon, Jean-Philippe ;

Pannecoucke, Xavier .

RSC ADVANCES, 2015, 5 (09) :6864-6868

[14] A mild and efficient synthesis of new pentafiuorosulfanyl-substituted electron-deficient alkenes and allylsilanes [J].

Falkowska, Ewelina ;

Suzenet, Franck ;

Jubault, Philippe ;

Bouillon, Jean-Philippe ;

Pannecoucke, Xavier .

TETRAHEDRON LETTERS, 2014, 55 (34) :4833-4836

[15] A molecular energy decomposition scheme for atoms in molecules [J].

Francisco, E ;

Pendás, AM ;

Blanco, MA .

JOURNAL OF CHEMICAL THEORY AND COMPUTATION, 2006, 2 (01) :90-102

[16] Optically active isoxazolidines via asymmetric cycloaddition reactions of nitrones with alkenes: Applications in organic synthesis [J].

Frederickson, M .

TETRAHEDRON, 1997, 53 (02) :403-425

[17]

Frisch M. J., 2016, GAUSSIAN 16

[18] THE PATH OF CHEMICAL-REACTIONS - THE IRC APPROACH [J].

FUKUI, K .

ACCOUNTS OF CHEMICAL RESEARCH, 1981, 14 (12) :363-368

[19] Conceptual density functional theory [J].

Geerlings, P ;

De Proft, F ;

Langenaeker, W .

CHEMICAL REVIEWS, 2003, 103 (05) :1793-1873

[20]

Gilmour R, 2014, CHIMIA, V68, P345

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