Preparation of Z-α,β-unsaturated diazoketones from aldehydes. Application in the construction of substituted dihydropyridin-3-ones.
The stereoselective preparation of α,β-unsaturated diazoketones with Z geometry is described from aldehydes and a new olefination reagent. When prepared from amino aldehydes, these diazoketones could be converted to substituted dihydropyridin-3-ones in just one step, after an intramolecular N-H insertion reaction. The straightforward synthesis of a natural trihydroxylated piperidine demonstrates the utility of these unsaturated diazoketones for the rapid construction of piperidines.
Instituto de Química de São Carlos, Universidade de São Paulo , CEP 13560-970, São Carlos, SP, Brazil.
Isac G
IG
Rosset
Antonio C B
AC
Burtoloso
D000447:Aldehydes / Q000737:chemistry*; D001391:Azo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011728:Pyridones / Q000138:chemical synthesis* / Q000737:chemistry
D000447:Aldehydes; D001391:Azo Compounds; D007659:Ketones; D011728:Pyridones