Synthesis of enantiopure cis- and trans-2,3-disubstituted piperidines.
The synthesis of enantiopure cis- and trans-2,3-disubstituted piperidines 4 is described. The key step of the synthesis involves the stereoselective reduction of chiral nonracemic lactams 2 by using BH3.Me2S. A rationalization of the stereoselectivity is presented.
Agami
Claude
C
Laboratoire de Synthèse Asymétrique (UMR CNRS 7611), Case courrier 47, Université P. et M. Curie, 4 place Jussieu, 75005 Paris, France.
Dechoux
Luc
L
Ménard
Cécilia
C
Hebbe
Séverine
S
D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D007202:Indicators and Reagents; D010880:Piperidines