Regioselective nucleophilic addition to pyridinium salts: a new route to substituted dihydropyridones.
The regioselective addition of nucleophiles to pyridinium salts generates an intermediate enol-ether, which can be hydrolyzed in situ to provide a range of dihydropyridones. Certain Grignards have shown inherent differences in the regioselectivity of addition to these salts, and this difference can be tuned to give single regioisomeric addition products. The dihydropyridone products can be further manipulated in many ways using standard transformations.
Donohoe
Timothy J
TJ
Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK. timothy.donohoe@chem.ox.ac.uk
Connolly
Matthew J
MJ
Walton
Lesley
L
D015394:Molecular Structure; D011726:Pyridinium Compounds / Q000737:chemistry*; D011728:Pyridones / Q000138:chemical synthesis* / Q000737:chemistry; D012492:Salts; D013237:Stereoisomerism
D011726:Pyridinium Compounds; D011728:Pyridones; D012492:Salts