Zn(II)-Catalyzed synthesis of piperidines from propargyl amines and cyclopropanes.
The reaction of benzyl-protected propargyl amines and 1,1-cyclopropane diesters in the presence of catalytic Zn(NTf(2))(2) allows access to highly functionalized piperidines in excellent yields. The process proceeds via a tandem cyclopropane ring-opening/Conia-ene cyclization.
Lebold
Terry P
TP
Department of Chemistry, The University of Western Ontario, London, Ontario, Canada N6A 5B7.
Leduc
Andrew B
AB
Kerr
Michael A
MA
D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D003521:Cyclopropanes / Q000737:chemistry*; D015394:Molecular Structure; D010293:Pargyline / Q000031:analogs & derivatives* / Q000737:chemistry; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D011437:Propylamines / Q000737:chemistry*; D015032:Zinc / Q000737:chemistry*
D003521:Cyclopropanes; D010880:Piperidines; D011437:Propylamines; C009054:propargylamine; D010293:Pargyline; D015032:Zinc