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Titolo:
Reaction of metallated tert-butyl(phenyl)phosphane oxide with electrophiles as a route to functionalized tertiary phosphane oxides: Alkylation reactions
Autore:
Haynes, RK; Au-Yeung, TL; Chan, WK; Lam, WL; Li, ZY; Yeung, LL; Chan, ASC; Li, P; Koen, M; Mitchell, CR; Vonwiller, SC;
Indirizzi:
Hong Kong Univ Sci & Technol, Dept Chem, Kowloon, Hong Kong, Peoples R China Hong Kong Univ Sci & Technol Kowloon Hong Kong Peoples R China s R China Hong Kong Polytech Univ, Dept Appl Biol & Chem Technol, Kowloon, Hong Kong, Peoples R China Hong Kong Polytech Univ Kowloon Hong Kong Peoples R China eoples R China Univ Sydney, Dept Organ Chem, Sydney, NSW 2006, Australia Univ Sydney Sydney NSW Australia 2006 n Chem, Sydney, NSW 2006, Australia
Titolo Testata:
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
fascicolo: 18, , anno: 2000,
pagine: 3205 - 3216
SICI:
1434-193X(200009):18<3205:ROMTOW>2.0.ZU;2-R
Fonte:
ISI
Lingua:
ENG
Soggetto:
BUTYLPHENYLPHOSPHINE OXIDE; ASYMMETRIC HYDROGENATION; STEREOSPECIFIC REDUCTION; BISPHOSPHINE LIGANDS; COMPLEXES; CATALYSTS; ACIDS; PHOSPHINITES; DERIVATIVES;
Keywords:
P-chiral phosphane oxides; alkylations; halides; metallations;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
57
Recensione:
Indirizzi per estratti:
Indirizzo: Haynes, RK Hong Kong Univ Sci & Technol, Dept Chem, Kowloon, Hong Kong, Peoples R China Hong Kong Univ Sci & Technol Kowloon Hong Kong Peoples R China
Citazione:
R.K. Haynes et al., "Reaction of metallated tert-butyl(phenyl)phosphane oxide with electrophiles as a route to functionalized tertiary phosphane oxides: Alkylation reactions", EUR J ORG C, (18), 2000, pp. 3205-3216

Abstract

P-Chiral tertiary phosphane oxides have been prepared from each of the secondary phosphane oxides racemic 1, (S-p)-(-)-4 and (R-p)-(+)-tert-butylphenylphosphane oxide (5) by lithiation with LDA or nBuLi, or sodiation with sodium hydride, in THF, and then by treatment with a series of primary alkyl halides. Doubly P-chiral ditertiary bis(phosphane oxides) are also obtainedfrom these metallated secondary phosphane oxides by treatment with electrophiles based on straight-chain, tartrate-derived, and bishalomethylarene dihalides. In general, the bis-phosphane oxides are obtained in good yields. However, when the alpha,omega-dihalide bears an embedded heteroatom (O or Si), yields are diminished. The enantiomeric purity of each of the products was assessed through admixture with (R-p)- and (S-p)-tert-butyl(phenyl)phosphanylthioic acids and measurement of the tert-butyl resonances in the H-1-NMR spectra. In all cases, the act of metallation of the enantiomerically pure secondary phosphane oxide followed by its alkylation is not accompaniedby detectable racemization. This method for preparing P-chiral tertiary phosphane oxides is therefore more straightforward than those described previously.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 21/09/20 alle ore 03:55:32