Complexation promoted additions to N-benzoyliminopyridinium ylides. A novel and highly regioselective approach to polysubstituted piperidines.
Unprecedented regioselectivities were observed for the addition of different organometallic nucleophiles to N-benzoyliminopyridinium ylides. Even benzylic and branched aliphatic Grignard reagents, which usually give substantial amounts of 1,4-adducts, showed excellent 1,2-regioselectivities. The electronic nature of the pyridinium ylide is taken into account to explain these results.
Legault
Claude
C
Département de Chimie, Université de Montréal, P.O. Box 6128, Station Downtown, Montréal, QC H3C 3J7, Canada.
Charette
André B
AB
D018360:Crystallography, X-Ray; D010880:Piperidines / Q000138:chemical synthesis*; D011726:Pyridinium Compounds / Q000737:chemistry*
D010880:Piperidines; D011726:Pyridinium Compounds