The synthesis of terminal oxazolinyloxiranes, even in enantioenriched form, has been performed byDarzens-type reaction of lithiated chloroalkyloxazolines with benzotriazolylmethanol (BtCH2OH) or bychloromethylation of 2-acyl-2-oxazolines. The synthetic utility of such oxiranes based on their ability toact either as electrophiles, undergoing ring-opening reactions with nucleophiles, or as nucleophiles inform of the oxiranyl anions, generated by stereoselective beta-deprotonation, has been investigated.
Terminal oxazolinyloxiranes: synthesis, reaction with amines and regioselective beta-lithiation
CARLUCCI, CLAUDIA;
2009-01-01
Abstract
The synthesis of terminal oxazolinyloxiranes, even in enantioenriched form, has been performed byDarzens-type reaction of lithiated chloroalkyloxazolines with benzotriazolylmethanol (BtCH2OH) or bychloromethylation of 2-acyl-2-oxazolines. The synthetic utility of such oxiranes based on their ability toact either as electrophiles, undergoing ring-opening reactions with nucleophiles, or as nucleophiles inform of the oxiranyl anions, generated by stereoselective beta-deprotonation, has been investigated.File in questo prodotto:
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