Enantioselective synthesis of 2-arylpiperidines from chiral lactams. A concise synthesis of (-)-anabasine.
Cyclodehydration of achiral or racemic aryl-delta-oxoacids with (R)-phenylglycinol stereoselectively affords chiral non-racemic bicyclic lactams, from which the enantiodivergent synthesis of (R)- and (S)-2-phenylpiperidine, the diastereodivergent synthesis of cis- and trans-3-ethyl-2-phenylpiperidine, and the enantioselective synthesis of the piperidine alkaloid (-)-anabasine is reported.
Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona, 08028-Barcelona, Spain. amat@farmacia.far.ub.es
Mercedes
M
Amat
Margalida
M
Cantó
Núria
N
Llor
Joan
J
Bosch
D000691:Anabasine / Q000138:chemical synthesis*; D007306:Insecticides / Q000138:chemical synthesis*; D007769:Lactams / Q000737:chemistry; D010880:Piperidines / Q000138:chemical synthesis; D010944:Plants; D013237:Stereoisomerism
D007306:Insecticides; D007769:Lactams; D010880:Piperidines; D000691:Anabasine