192937-72-7Relevant academic research and scientific papers
Alkylation of chiral 2-(aminomethyl)oxazolines
Bail, Marc Le,Aitken, David J.,Vergne, Fabrice,Husson, Henri-Philippe
, p. 1681 - 1690 (2007/10/03)
Chiral 2-(aminomethyl)oxazolines 3 and 7, in wich the heterocycle is derived from (R)-phenylglycinol, are synthesized and studied in alkylation reactions involving strong base and alkyl halides.The tertiary amine derivative 3 is alkylated efficiently at the α-carbon centre with no stereochemical induction, while the tertiary carbamate 7 is alkylated in moderate yield and reasonable diastereomeric excess.The stereochemical control observed in the latter case can be explained by the preferred formation of an E-enolate during the deprotonation step by prior complexation of the carbaamate carbonyl group to the base.
