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Titolo:
Synthesis of silyl enol ethers and their aldol reaction utilizing 2,5-diphenyl-1-silacyclopentene and 2,5-diphenyl-1-sila-3-cyclopentene derivatives
Autore:
Nagao, Y; Tanaka, N; Namiki, N; Kozawa, K;
Indirizzi:
Sci Univ Tokyo, Fac Sci & Technol, Dept Ind Chem, Noda, Chiba 2788510, Japan Sci Univ Tokyo Noda Chiba Japan 2788510 Chem, Noda, Chiba 2788510, Japan
Titolo Testata:
NIPPON KAGAKU KAISHI
fascicolo: 6, , anno: 2001,
pagine: 355 - 361
SICI:
0369-4577(200106):6<355:SOSEEA>2.0.ZU;2-8
Fonte:
ISI
Lingua:
JPN
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
5
Recensione:
Indirizzi per estratti:
Indirizzo: Nagao, Y Sci Univ Tokyo, Fac Sci & Technol, Dept Ind Chem, Noda, Chiba 2788510, Japan Sci Univ Tokyo Noda Chiba Japan 2788510 da, Chiba 2788510, Japan
Citazione:
Y. Nagao et al., "Synthesis of silyl enol ethers and their aldol reaction utilizing 2,5-diphenyl-1-silacyclopentene and 2,5-diphenyl-1-sila-3-cyclopentene derivatives", NIP KAG KAI, (6), 2001, pp. 355-361

Abstract

Silyl enol ethers were prepared by the reaction of ketones with r-1, t-2, t-5- and r-1, t-2, c-5-isomeric mixture of 1-chloro-2, 5-dimethyl-1-phenyl-1-silacyclopentane and 1-alkyl-1-chloro-2,5-diphenyl-1-sila-3-cyclopentene,and their aldol reaction was investigated. The silyl enol ethers were prepared in the presence of triethylamine as base in N, N-dimethylformamide (DMF)or LDA as base in THF. The isomer ratio oi the silyl enol ethers implied that retention occurred on Si-substitution in the presence of triethylamineand some inversion occurred on Si-substitution in LDA. The aldol reaction of these silyl enol ethers were investigated by a reaction with benzaldehyde in the presence of titanium tetrachloride. The aldol products were separated by a column chromatography using silica gel, and obtained as the diastereomers of (R*, R*) and (R*, S*) forms. The silyl enol ethers from 1-chloro-2,5-dimethyl-1-phenyl-1-silacyclopentane gave more (R*, R*)form, and the enol ethers from 1-alkyl-1-chloro-2,5-diphenyl-1-sila-3-cyclopentene gave (R*, R*) form selectively.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 05/12/20 alle ore 19:09:27