Stereoselective Capture of <i>N</i>‑Acyliminium
Ions Generated from α‑Hydroxy‑<i>N</i>‑acylcarbamides: Direct Synthesis of Uracils from Barbituric
Acids Enabled by SmI<sub>2</sub> Reduction
Michal Szostak
Brice Sautier
David J. Procter
10.1021/ol403340j.s001
https://acs.figshare.com/articles/journal_contribution/Stereoselective_Capture_of_i_N_i_Acyl_iminium_Ions_Generated_from_Hydroxy_i_N_i_acyl_carbamides_Direct_Synthesis_of_Uracils_from_Barbituric_Acids_Enabled_by_SmI_sub_2_sub_Reduction/2027817
Lewis 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 <i>N</i>-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.
2015-12-17 00:17:38
Barbituric Acids Enabled
SmI 2 ReductionLewis acid
barbituric acids