Szostak, Michal Sautier, Brice Procter, David J. 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 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. Barbituric Acids Enabled;SmI 2 ReductionLewis acid;barbituric acids 2015-12-17
    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
10.1021/ol403340j.s001