2,6-Disubstituted and 2,2,6-trisubstituted piperidines from serine: asymmetric synthesis and further elaboration.
4-Hydroxy-3,4-dihydro-2H-pyridine-1-carboxylic acid benzyl esters, which are readily prepared from serine and terminal acetylenes, undergo Claisen rearrangement to piperidine derivatives when heated with butyl vinyl ether in the presence of Hg(OAc)(2) and Et(3)N. This route to optically pure piperidines having substituents alpha to nitrogen is general, and the rearrangement products are versatile intermediates for making a broad range of amines containing a substituted piperidine subunit.
Acharya
Hukum P
HP
Department of Chemistry, University of Alberta, Edmonton, Alberta T6G 2G2, Canada.
Clive
Derrick L J
DL
D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D012694:Serine / Q000737:chemistry*; D017550:Spectroscopy, Fourier Transform Infrared
D010880:Piperidines; D012694:Serine