Highly enantioselective access to primary propargylamines: 4-piperidinone as a convenient protecting group.
[reaction: see text] We report a highly enantioselective, catalytic three-component coupling of aldehydes, alkynes, and 4-piperidone hydrochloride hydrate to afford the corresponding tertiary propargylamines in useful yields. The selective cleavage of the piperidone protecting group using either ammonia/EtOH or a polymer-supported scavenger amine furnishes primary propargylamines.
Aschwanden
Patrick
P
Laboratorium für Organische Chemie, ETH Zurich, Switzerland.
Stephenson
Corey R J
CR
Carreira
Erick M
EM
D000447:Aldehydes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D010293:Pargyline / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D010881:Piperidones / Q000737:chemistry*; D011437:Propylamines / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000447:Aldehydes; D000480:Alkynes; D010881:Piperidones; D011437:Propylamines; C009054:propargylamine; D010293:Pargyline