Terminal oxazolinyloxiranes: synthesis, reaction with amines and regioselective β-lithiation

L Degennaro, V Capriati, C Carlucci, S Florio, R Luisi…

Index: Degennaro, Leonardo; Capriati, Vito; Carlucci, Claudia; Florio, Saverio; Luisi, Renzo; Nuzzo, Irene; Cuocci, Corrado Tetrahedron, 2009 , vol. 65, # 42 p. 8745 - 8755

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Citation Number: 10

Abstract

The synthesis of terminal oxazolinyloxiranes, even in enantioenriched form, has been performed by Darzens-type reaction of lithiated chloroalkyloxazolines with benzotriazolylmethanol (BtCH2OH) or by chloromethylation of 2-acyl-2-oxazolines. The synthetic utility of such oxiranes based on their ability to act either as electrophiles, undergoing ring-opening reactions with nucleophiles, or as nucleophiles in form of the ...