Michael-Stork addition of cyclopentyl enamine to allenyl ketones and esters.
[Chemical reaction: see text] We report the first examples of a Michael-Stork enamine addition to allenyl esters and ketones. Studies reveal that 2 equivalents of enamine are required for optimal yields. In the case of an allenyl methyl ketone, cyclopentyl enamine addition led to 8-oxobicyclo[3.2.1]octane formation, providing evidence for the in situ formation of an enamine intermediate following the initial Michael-Stork reaction.
Silvestri
Maximilian A
MA
Department of Chemistry, Florida Atlantic University, Boca Raton, Florida 33431-0991, USA.
Bromfield
Deborah C
DC
Lepore
Salvatore D
SD
D003517:Cyclopentanes / Q000737:chemistry*; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D011725:Pyridines / Q000737:chemistry*
D003517:Cyclopentanes; D004952:Esters; D007202:Indicators and Reagents; D007659:Ketones; D011725:Pyridines; C511582:cyclopentyl enamine