Synthesis of N-Cbz-Substituted beta(3)-Amino Ketones Utilizing 4-Substituted 1,3-Oxazinan-6-ones
Brad E Sleebs, Nghi H Nguyen, Andrew B Hughes
Synlett | GEORG THIEME VERLAG KG | Published : 2013
Stereoselective synthesis of N-Cbz-substituted β-amino ketones exploiting the versatile 1,3-oxazin-6-one scaffold is reported. The 4-substituted 1,3-oxazinan-6-ones were enolized and acylated diastereoselectively by addition of various acyl halides. Acidic decarboxylation was then employed to smoothly transform the 5-acylated products to chiral β-amino ketones. This methodology further highlights the utility of the 1,3-oxazinan-6-one as a scaffold to access valuable synthons that are used in the peptidomimetic field. © Georg Thieme Verlag Stuttgart · New York.
Awarded by NHMRC
We thank La Trobe University for the provision of a postgraduate scholarship awarded to N.H.N. and the NHMRC (App. 1010326) for funding B.E.S.