title: Stereoselective trans- and cis-dihydroxylations of 2H-pyranyl and dihydropyridinyl heterocycles synthesized from formal [3 + 3]-cycloaddition reactions of alpha,beta-unsaturated iminium ions with 1,3-dicarbonyl equivalents.
abstract: [reaction: see text]We describe here an inherent problem in direct epoxidation of the endocyclic olefin in 2H-pyrans fused to 2-pyrones. Such difficulties led to the development of highly stereoselective trans- and cis-dihydroxylations of these olefinic systems in both 2H-pyrans and dihydropyridines fused to a 2-pyrones or a 2-cyclohexenone. Protocols for the removal of the activated allylic hydroxyl group are also reported.
authors: Department of Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, USA.
authors: L R
authors: LR
authors: Zehnder
authors: L L
authors: LL
authors: Wei
authors: R P
authors: RP
authors: Hsung
authors: K P
authors: KP
authors: Cole
authors: M J
authors: MJ
authors: McLaughlin
authors: H C
authors: HC
authors: Shen
authors: H M
authors: HM
authors: Sklenicka
authors: J
authors: J
authors: Wang
authors: C A
authors: CA
authors: Zificsak
mesh_terms: D000470:Alkaloids / Q000737:chemistry; D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D003512:Cyclohexanones / Q000737:chemistry; D006574:Heterocyclic Compounds, 2-Ring / Q000138:chemical synthesis* / Q000737:chemistry*; D006900:Hydroxylation; D007097:Imines / Q000737:chemistry; D015394:Molecular Structure; D011714:Pyrans / Q000737:chemistry; D011725:Pyridines / Q000737:chemistry; D011753:Pyrones / Q000737:chemistry*; D011804:Quinolines; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000470:Alkaloids; D000475:Alkenes; D003512:Cyclohexanones; D006574:Heterocyclic Compounds, 2-Ring; D007097:Imines; D011714:Pyrans; D011725:Pyridines; D011753:Pyrones; D011804:Quinolines; C432303:arisugacin A; C432304:arisugacin H; C432305:lepadin A; C432306:orevactaene; C036468:cyclohexanone