The synthesis of terminal oxazolinyloxiranes, even in enantioenriched form, has been performed by Darzens-type reaction of lithiated chloroalkyloxazolines with benzotriazolylmethanol (BtCH(2)OH) 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 oxiranyl anions, generated by stereoselective beta-deprotonation, has been investigated. (C) 2009 Elsevier Ltd. All rights reserved
Terminal oxazolinyloxiranes: synthesis, reaction with amines and regioselective b-lithiation
Cuocci C
2009
Abstract
The synthesis of terminal oxazolinyloxiranes, even in enantioenriched form, has been performed by Darzens-type reaction of lithiated chloroalkyloxazolines with benzotriazolylmethanol (BtCH(2)OH) 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 oxiranyl anions, generated by stereoselective beta-deprotonation, has been investigated. (C) 2009 Elsevier Ltd. All rights reservedFile in questo prodotto:
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