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Titolo:
LEWIS-ACID-MEDIATED AND CATIONIC LITHIUM-MEDIATED DIASTEREOSELECTIVE ALDOL-TYPE REACTION-BASED ON A DOUBLE CHIRAL RECOGNITION MANNER FOR THE ASYMMETRIC-SYNTHESIS OF ALPHA-SUBSTITUTED SERINES
Autore:
SANO S; LIU XK; TAKEBAYASHI M; KOBAYASHI Y; TABATA K; SHIRO M; NAGAO Y;
Indirizzi:
UNIV TOKUSHIMA,FAC PHARMACEUT SCI,SHOMACHI 1-78 TOKUSHIMA 770 JAPAN UNIV TOKUSHIMA,FAC PHARMACEUT SCI TOKUSHIMA 770 JAPAN RIGAKU CORP AKISHIMA TOKYO 196 JAPAN
Titolo Testata:
Tetrahedron letters
fascicolo: 23, volume: 36, anno: 1995,
pagine: 4101 - 4104
SICI:
0040-4039(1995)36:23<4101:LACLDA>2.0.ZU;2-R
Fonte:
ISI
Lingua:
ENG
Soggetto:
AMINO-ACIDS;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
12
Recensione:
Indirizzi per estratti:
Citazione:
S. Sano et al., "LEWIS-ACID-MEDIATED AND CATIONIC LITHIUM-MEDIATED DIASTEREOSELECTIVE ALDOL-TYPE REACTION-BASED ON A DOUBLE CHIRAL RECOGNITION MANNER FOR THE ASYMMETRIC-SYNTHESIS OF ALPHA-SUBSTITUTED SERINES", Tetrahedron letters, 36(23), 1995, pp. 4101-4104

Abstract

Diastereoselective aldol-type reaction of ethyl (5R or hoxy-2,5-dihydro-5-isopropyl-2-pyrazinecarboxylate (5) with chiral aldehyde 7 was investigated by using Sn(OSO2CF3)(2)-N-ethylpiperizine, MgBr2-Et(3)N, n-butyllithium, and lithium diisopropylamide. The mediation mode with Sn(II) between (5R or 5S)-5 and 7 proved to be quite different from thatwith Mg(II). The two aldol products were converted to the corresponding gamma-lactonic alpha-substituted serines (2S)- and (2R)-10.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 05/07/20 alle ore 22:33:13