Pyrones to pyrans: enantioselective radical additions to acyloxy pyrones.
This paper describes a highly site-, diastereo-, and enantioselective intermolecular radical addition/hydrogen atom transfer to hydroxypyrone pyromeconic and kojic acids. The methodology can be extended to the formation of chiral quaternary centers. The products obtained are densely functionalized pyran moieties. The products contain structural features amenable for the introduction of additional substituents.
Sibi
Mukund P
MP
Department of Chemistry, North Dakota State University, Fargo, ND 58105, USA. mukund.sibi@ndsu.edu
Zimmerman
Jake
J
D000215:Acylation; D001565:Benzoates / Q000737:chemistry; D005609:Free Radicals / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D010100:Oxygen / Q000737:chemistry; D010421:Pentanoic Acids / Q000737:chemistry; D011714:Pyrans / Q000138:chemical synthesis*; D011753:Pyrones / Q000138:chemical synthesis*; D013237:Stereoisomerism
D001565:Benzoates; D005609:Free Radicals; D010421:Pentanoic Acids; D011714:Pyrans; D011753:Pyrones; C005566:pivalic acid; C012018:pyromellitic acid; D010100:Oxygen