title: Diels-Alder reactions of N-acyl-2-alkyl(aryl)-5-vinyl-2,3-dihydro-4-pyridones.
abstract: Readily available N-acyl-5-vinyl-2,3-dihydro-4-pyridones undergo Diels-Alder cyclization with various dienophiles to afford novel octahydroquinolines containing synthetically useful functionality. With dihydropyridone 5 and cis-disubstituted dienophiles, the resulting cycloadducts were obtained as single diastereomers in good to excellent yield. The corresponding reaction of 5 with methyl acrylate, acrylonitrile, and phenyl vinyl sulfone showed modest preference for the endo adducts. The effect of the dihydropyridone C-2 and C-4 substituents on the degree of diastereofacial control was examined. By using this methodology, the core decahydroquinoline skeleton of gephyrotoxin was prepared in a stereocontrolled fashion. Interesting reactivity was observed with certain dienophiles leading to ring-opening of the initially formed cycloadducts. This tandem reaction provides a route to uniquely substituted beta-aminoketones, alcohols, and unnatural amino acids.
authors.affiliation: Department of Chemistry, North Carolina State University, Raleigh, NC 27695-8204, USA. daniel_comins@ncsu.edu
authors.forename: Daniel L
authors.initials: DL
authors.lastname: Comins
authors.forename: Jeffrey T
authors.initials: JT
authors.lastname: Kuethe
authors.forename: Teresa M
authors.initials: TM
authors.lastname: Miller
authors.forename: Florence C
authors.initials: FC
authors.lastname: Février
authors.forename: Clinton A
authors.initials: CA
authors.lastname: Brooks
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis*; D000596:Amino Acids / Q000138:chemical synthesis*; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D007659:Ketones / Q000138:chemical synthesis*; D015394:Molecular Structure; D011728:Pyridones / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D000596:Amino Acids; D007659:Ketones; D011728:Pyridones