Synthesis of N-Cbz-Substituted β3-Amino Ketones Utilizing 4-Substituted 1,3-Oxazinan-6-ones

Abstract 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...

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Bibliographic Details
Published in:Synlett 2013-04, Vol.24 (7), p.823-826
Main Authors: Sleebs, Brad E., Nguyen, Nghi H., Hughes, Andrew B.
Format: Article
Language:English
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Summary:Abstract 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.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0032-1318345