Synthesis of N-Cbz-Substituted beta(3)-Amino Ketones Utilizing 4-Substituted 1,3-Oxazinan-6-ones
- Author(s)
- Sleebs, BE; Nguyen, NH; Hughes, AB;
- Journal Title
- SYNLETT
- Publication Type
- Journal Article
- Abstract
- Stereoselective synthesis of N-Cbz-substituted beta-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 beta-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.
- Publisher
- GEORG THIEME VERLAG KG
- Keywords
- ketones ; amino acids ; acylation ; ring opening ; oxazinanones
- Research Division(s)
- Chemical Biology
- Publisher's Version
- https://doi.org/10.1055/s-0032-1318345
- Terms of Use/Rights Notice
- © 2012 Georg Thieme Verlag KG
Creation Date: 2013-04-01 12:00:00
Last Modified: 2014-12-11 02:31:23