Asymmetric synthesis and stereochemistry of chiral cis- and trans-3-alkyl-4-aminopiperidines

Autor:	M. Yu. Antipin, A. A. Borisenko, G. V. Grishina, E. R. Luk'yanenko
Rok vydání:	2012
Předmět:	chemistry.chemical_classification Steric effects chemistry.chemical_compound chemistry Metalation Stereochemistry Organic Chemistry Absolute configuration Enantioselective synthesis Alkylation Alkyl Cis–trans isomerism Raney nickel
Zdroj:	Chemistry of Heterocyclic Compounds. 48:733-747
ISSN:	1573-8353 0009-3122
DOI:	10.1007/s10593-012-1052-9
Popis:	Chiral nonracemic 3-substituted cis- and trans-4-aminopiperidines, which are precursors of anilidopiperidine analgesics, were obtained by diastereoselective synthesis from 1-methyl- and 1-benzyl-4-[(S)-1-phenylethyl]iminopiperidines, using the following reaction sequence: metalation with lithium diethylamide, alkylation with alkyl halides, and hydride reduction or hydrogenation over Raney nickel. The steric direction of the reaction, three-dimensional structure, preferred conformation, and absolute configuration of the resultant aminopiperidines were determined.
Databáze:	OpenAIRE
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