A concise approach to 2-azabicyclo[3.3.1]nonane derivatives from an acyclic precursor.
[Reaction: see text]. Condensation of a readily available 5-amino-2-alkenoate ester with alpha-unsubstituted aliphatic aldehydes leads to substituted 1,2,3,4-tetrahydropyridines. Subsequent manipulation of the ester and enamine functions gives a quick access to 2-azabicyclo[3.3.1]nonane-containing compounds.
Aurrecoechea
José M
JM
Departamento de Química Orgánica II, Facultad de Ciencia y Tecnología, Universidad del País Vasco, Apartado 644, 48080 Bilbao, Spain. jm.aurrecoechea@ehu.es
Gorgojo
José M
JM
Saornil
Carlos
C
D000447:Aldehydes / Q000737:chemistry; D000473:Alkanes / Q000138:chemical synthesis* / Q000737:chemistry; D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D004952:Esters / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000447:Aldehydes; D000473:Alkanes; D001372:Aza Compounds; D001643:Bridged Bicyclo Compounds; D004952:Esters; C017573:nonane