title: Stereoselective capture of N-acyliminium ions generated from α-hydroxy-N-acylcarbamides: direct synthesis of uracils from barbituric acids enabled by SmI2 reduction.
abstract: 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 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.
authors.affiliation: School of Chemistry, University of Manchester , Oxford Road, Manchester, M13 9PL, U.K.
authors.forename: Michal
authors.initials: M
authors.lastname: Szostak
authors.forename: Brice
authors.initials: B
authors.lastname: Sautier
authors.forename: David J
authors.initials: DJ
authors.lastname: Procter
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis; D000605:Amino Alcohols / Q000737:chemistry*; D001463:Barbiturates / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D007097:Imines / Q000737:chemistry; D007477:Ions; D058116:Lewis Acids / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D014498:Uracil / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000596:Amino Acids; D000605:Amino Alcohols; D001463:Barbiturates; D007097:Imines; D007477:Ions; D058116:Lewis Acids; D014498:Uracil; C032232:barbituric acid