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Titolo:
ASYMMETRIC-SYNTHESIS .39. SYNTHESIS OF 2-(1-AMINOALKYL)PIPERIDINES VIA 2-CYANO-6-PHENYL OXAZOLOPIPERIDINE
Autore:
FROELICH O; DESOS P; BONIN M; QUIRION JC; HUSSON HP; ZHU JP;
Indirizzi:
UNIV PARIS 05,FAC SCI PHARMACEUT & BIOL,CNRS,CHIM THERAPEUT LAB,4 AVEOBSERV F-75270 PARIS 06 FRANCE UNIV PARIS 05,FAC SCI PHARMACEUT & BIOL,CNRS,CHIM THERAPEUT LAB F-75270 PARIS 06 FRANCE CNRS,INST CHIM SUBST NAT F-91198 GIF SUR YVETTE FRANCE
Titolo Testata:
Journal of organic chemistry
fascicolo: 19, volume: 61, anno: 1996,
pagine: 6700 - 6705
SICI:
0022-3263(1996)61:19<6700:A.SO2V>2.0.ZU;2-R
Fonte:
ISI
Lingua:
ENG
Soggetto:
CN(R,S) METHOD; DERIVATIVES; PIPERIDINES; (+)-CONIINE; AGONISTS; LIGANDS;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
30
Recensione:
Indirizzi per estratti:
Citazione:
O. Froelich et al., "ASYMMETRIC-SYNTHESIS .39. SYNTHESIS OF 2-(1-AMINOALKYL)PIPERIDINES VIA 2-CYANO-6-PHENYL OXAZOLOPIPERIDINE", Journal of organic chemistry, 61(19), 1996, pp. 6700-6705

Abstract

The asymmetric synthesis of a series of 2-(1-aminoalkyl) piperidines using (-)-2-cyano-6-phenyloxazolopiperidine 1 is described. LiAlH4 reduction of 1 followed by hydrogenolysis led to the diamine 3. The same strategy applied to C-2-methylated compound 7 afforded [(2S)-2-methylpiperidin-2-yl]methanamine (9). Addition of lithium derivatives to the cyano group of 1 resulted in the formation of an intermediate imino bicyclic system (11a-c) which could be diastereoselectively reduced to substituted diamino alcohols 13a-c. The addition of an excess of PhLi to 1 in the presence of LiBr furnished disubstituted amine 19, the precursor of diphenyl[(2S)-piperidin-2-yl]methanamine (22).

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Documento generato il 01/10/20 alle ore 03:58:43