ol403340j_si_001.pdf (4.05 MB)
Stereoselective Capture of N‑Acyliminium Ions Generated from α‑Hydroxy‑N‑acylcarbamides: Direct Synthesis of Uracils from Barbituric Acids Enabled by SmI2 Reduction
journal contribution
posted on 2015-12-17, 00:17 authored by Michal Szostak, Brice Sautier, David J. ProcterLewis acid promoted
cleavage of α-amino alcohols derived
from barbituric acids via chemoselective Sm(II)-mediated electron
transfer affords a wide range of C6-substituted 5,6-dihydrouracils.
The reaction involves the first generation of N-acyliminium
ions directly from the versatile barbituric acids and proceeds with
excellent stereoselectivity. The products are shown to be active in
generic transition metal catalyzed reactions, thus providing a modular
and highly practical sequence to the biologically significant uracil
derivatives.