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Titolo:
Deracemization of alkyl diarylmethanes using (-)-sparteine or a chiral proton source
Autore:
Prat, L; Dupas, G; Duflos, J; Queguiner, G; Bourguignon, J; Levacher, V;
Indirizzi:
INSA, IRCOF, CNRS, Lab Chim Organ Fine & Heterocycl, F-76131 Mt St Aignan,France INSA Mt St Aignan France F-76131 Heterocycl, F-76131 Mt St Aignan,France
Titolo Testata:
TETRAHEDRON LETTERS
fascicolo: 27, volume: 42, anno: 2001,
pagine: 4515 - 4518
SICI:
0040-4039(20010702)42:27<4515:DOADU(>2.0.ZU;2-X
Fonte:
ISI
Lingua:
ENG
Soggetto:
ENANTIOSELECTIVE PROTONATION; ANILINE; ACID;
Keywords:
deracemization; asymmetric protonation; (-)-sparteine; chiral proton donor;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
16
Recensione:
Indirizzi per estratti:
Indirizzo: Levacher, V INSA, IRCOF, CNRS, Lab Chim Organ Fine & Heterocycl, Rue Tenieres BP 08, F-76131 Mt St Aignan, France INSA Rue Tenieres BP 08 Mt St Aignan France F-76131 n, France
Citazione:
L. Prat et al., "Deracemization of alkyl diarylmethanes using (-)-sparteine or a chiral proton source", TETRAHEDR L, 42(27), 2001, pp. 4515-4518

Abstract

In a first stage, deracemization of 2-(1-phenylethyl)pyridine 1 and chlorpheniramine 2 was investigated in the presence of (-)-sparteine as a chilal ligand. Whereas (R)-2-(1-phenylethyl)pyridine 1 was obtained in 65% ee with2,6-di-tert-bulyl-4-methylphenol as a proton donor, the opposite stereoselection was observed with EtOH leading to (S)-2-(1-phenylethyl)pyridine 1 in53% ee, A second methodology making use of (+)-(R)-1-[5-chloro-2-(methylarnino)-phenyl]-1,2,3,4-tetrahydroisoquinoline 4 as a chiral proton source gave higher enantioselectivities, affording (R)-1 and (R)-2 in up to 84 and 75% ee, respectively. (C) 2001 Elsevier Science Ltd. All rights reserved.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 20/01/20 alle ore 22:59:03