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

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