Title: Opposite Regioselectivity in the Sequential Ring-Opening of 2-(Alkanoyloxymethyl)aziridinium Salts by Bromide and Fluoride in the Synthesis of Functionalized β-Fluoro Amines
Abstract: 1-Arylmethyl-2-(bromomethyl)aziridines were converted into the corresponding 2-(alkanoyloxymethyl)aziridines upon treatment with potassium 2-methylpropanoate or potassium 2-methylbutyrate in DMSO in excellent yields, following regioselective ring-opening towards N-(2-bromo-3-alkanoyloxypropyl)amines using allyl bromide or an arylmethyl bromide in acetonitrile. Treatment of the latter β-bromo amines with tetrabutylammonium fluoride in acetonitrile afforded 2-amino-1-fluoropropanes as the major compounds (72-86%) besides the isomeric 1-amino-2-fluoropropanes in minor quantities (14-28%). The ring-opening of the intermediate aziridinium salts by bromide and fluoride in acetonitrile resulted in a different regioselectivity with a preferential attack of bromide at the more hindered carbon atom and of fluoride at the less hindered carbon atom of the aziridinium ion.
Publication Year: 2006
Publication Date: 2006-08-01
Language: en
Type: article
Indexed In: ['crossref']
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Cited By Count: 6
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