Novel Stereoselective Synthesis of Chiral Nonracemic cis- and trans-3-Alkyl-4-aminopiperidines.

Autor: Lukyanenko, E.R., Borisenko, A.A., Grishina, G.V.
Předmět:
Zdroj: Chemistry of Heterocyclic Compounds; Apr2004, Vol. 40 Issue 4, p525-527, 3p
Abstrakt: Discusses a study which showed that previously unknown optically pure trans-(3R,4R) isomers 4a-d with diastereomeric excess and the diastereomeric pair of cis-(3S,4R)-(3R,4S) isomers of N-[(1S)-1-phenylethyl]-4-amino-1,3-dialkylpiperidine are formed in yield by sequential lithiation and alkylation by alkyl halides of the chiral imines. Separation of the cis isomers 3a-d and the trans isomers 4a-d by column chromatography on aluminum oxide; Establishment of the cis and trans structure of isomers 3a-d and 4a-d by analysis of the vicinal spin-spin coupling constants for the 3-H and 4-H protons of the piperidine ring.
Databáze: Complementary Index