Synthesis of fluorinated allylic amines: Reaction of 2-(trimethylsilyl)ethyl sulfones and sulfoxides with fluorinated imines

A new synthesis of fluorinated allylamines through the reaction of 2-(trimethylsilyl)ethyl sulfones and sulfoxides with imines and imino esters is described. ▪ A new synthesis of fluorinated allylamines through the reaction of 2-(trimethylsilyl)ethyl sulfones and sulfoxides (as vinyl anion equivalen...

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Bibliographic Details
Published in:Journal of fluorine chemistry 2007-10, Vol.128 (10), p.1248-1254
Main Authors: Fustero, Santos, Flores, Sonia, Cuñat, Ana C., Jiménez, Diego, del Pozo, Carlos, Bueno, Jorge, Sanz-Cervera, Juan F.
Format: Article
Language:English
Subjects:
2-(Trimethylsilyl)ethyl sulfones and sulfoxides
Fluorinated allylamines
Fluorinated imines
Fluorinated imino esters
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Summary:A new synthesis of fluorinated allylamines through the reaction of 2-(trimethylsilyl)ethyl sulfones and sulfoxides with imines and imino esters is described. ▪ A new synthesis of fluorinated allylamines through the reaction of 2-(trimethylsilyl)ethyl sulfones and sulfoxides (as vinyl anion equivalents) with imines and imino esters has been described. The process includes a TBAF-mediated fragmentation of 2-(trimethylsilyl)ethyl sulfones to afford the desired allylic amines. When the reaction is performed with the corresponding sulfoxides, the fragmentation takes place under the addition conditions, affording the final products in a single step.
ISSN:0022-1139
1873-3328
DOI:10.1016/j.jfluchem.2007.05.006