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Titolo:
Electrogenerated chiral 4-methoxy-2-oxazolidinones as diastereoselective amidoalkylation reagents for the synthesis of beta-amino alcohol precursors
Autore:
Schierle-Arndt, K; Kolter, D; Danielmeier, K; Steckhan, E;
Indirizzi:
Univ Bonn, Kekule Inst Organ Chem & Biochem, D-53121 Bonn, Germany Univ Bonn Bonn Germany D-53121 gan Chem & Biochem, D-53121 Bonn, Germany
Titolo Testata:
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
fascicolo: 13, , anno: 2001,
pagine: 2425 - 2433
SICI:
1434-193X(200107):13<2425:EC4ADA>2.0.ZU;2-J
Fonte:
ISI
Lingua:
ENG
Soggetto:
KEY BUILDING-BLOCK; HIGHLY STEREOSELECTIVE SYNTHESIS; HIV-PROTEASE INHIBITORS; RING-CLOSING METATHESIS; N-ACYLIMINIUM IONS; OLEFIN METATHESIS; ENANTIOSELECTIVE SYNTHESIS; ORGANOCOPPER REAGENTS; ORGANOZINC REAGENTS; NITROALDOL REACTION;
Keywords:
amidoalkylation; amino alcohols; metathesis; nucleophilic exchange; oxazolidinone;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
74
Recensione:
Indirizzi per estratti:
Indirizzo: Kolter, D Forschungszentrum Julich GmbH, Inst Biotechnol 2, D-52425 Julich, Germany Forschungszentrum Julich GmbH Julich Germany D-52425 , Germany
Citazione:
K. Schierle-Arndt et al., "Electrogenerated chiral 4-methoxy-2-oxazolidinones as diastereoselective amidoalkylation reagents for the synthesis of beta-amino alcohol precursors", EUR J ORG C, (13), 2001, pp. 2425-2433

Abstract

A flexible and efficient synthesis of enantiomerically pure 4,5-substituted 2-oxazolidinones - important target molecules as precursors of pharmacologically active 2-oxazolidinones, p-amino alcohols, P-blockers and azasugar derivatives - is described. As starting materials, the enantiopure storage forms of chiral N-acyliminium ions (4RS,5S)-5-chloromethyl-4-methoxy-1,3-oxazolidin-2-one (2) and (4RS,5R)-4-methoxy-5-methyl-1,3-oxazolidin-2-one (3)were used; these are readily available from the chiral pool with the aid of electrochemical transformations. Substitution of the 4-methoxy group in building blocks 2 and 3 with a large variety of organometallic nucleophiles resulted in the trans-diastereoselective formation of enantiopure 4,5-disubstituted 2-oxazolidinones, with a high degree of flexibility in the substituent at the 4-position.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 06/04/20 alle ore 08:00:25