An enantioselective synthetic route to cis-2,4-disubstituted and 2,4-bridged piperidines.
A synthetic route to enantiopure cis-2,4-disubstituted and 2,4-bridged piperidines is reported, the key step being a stereoselective conjugate addition of an organocuprate to a phenylglycinol-derived unsaturated lactam bearing a substituent at the 8a-position.
Amat
Mercedes
M
Laboratory of Organic Chemistry, Faculty of Pharmacy, and Institute of Biomedicine (IBUB), University of Barcelona, 08028 Barcelona, Spain. amat@ub.edu
Pérez
Maria
M
Minaglia
Annamaria T
AT
Bosch
Joan
J
D003300:Copper / Q000737:chemistry*; D004983:Ethanolamines; D005998:Glycine / Q000031:analogs & derivatives* / Q000737:chemistry; D007769:Lactams / Q000737:chemistry*; D008956:Models, Chemical; D009942:Organometallic Compounds / Q000737:chemistry*; D010880:Piperidines / Q000138:chemical synthesis*; D013237:Stereoisomerism
D004983:Ethanolamines; D007769:Lactams; D009942:Organometallic Compounds; D010880:Piperidines; C005332:N-phenylethanolamine; D003300:Copper; D005998:Glycine