Synthesis of N-Cbz-Substituted ß³-Amino Ketones Utilizing 4-Substituted 1,3-Oxazinan-6-ones.

Autor: Sleebs, Brad E., Nguyen, Nghi H., Hughes, Andrew B.
Předmět:
Zdroj: Synlett; 4/15/2013, Vol. 24 Issue 7, p823-826, 4p
Abstrakt: Stereoselective synthesis of N-Cbz-substituted ß-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 ß-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. [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index