Enantioselective synthesis of functionalized medium-sized oxacycles.
Enantioselective routes to functionalized, seven-, eight-, and nine-membered oxacycles that are amenable to further elaboration have been developed. Salient features of the methodology include highly diastereoselective and regioselective transformations of an ephedrine-derived epoxy morpholinone to functionalized precursors of the oxacycles. The ephedrine scaffold exerts remote stereocontrol in the functionalization of the appended oxacycle. [reaction: see text]
Pansare
Sunil V
SV
Department of Chemistry, Memorial University of Newfoundland, St. John's, Newfoundland, Canada A1B 3X7. spansare@mun.ca
Adsool
Vikrant A
VA
D003500:Cyclization; D004583:Electrons; D006573:Heterocyclic Compounds, 1-Ring / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D007769:Lactams / Q000737:chemistry; D008094:Lithium / Q000737:chemistry; D008745:Methylation; D009525:Niacin / Q000737:chemistry; D009536:Niacinamide / Q000737:chemistry; D010880:Piperidines / Q000737:chemistry; D011725:Pyridines / Q000737:chemistry
D006573:Heterocyclic Compounds, 1-Ring; D007202:Indicators and Reagents; D007769:Lactams; D010880:Piperidines; D011725:Pyridines; D009536:Niacinamide; D009525:Niacin; D008094:Lithium