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Titolo:
Development and application of enantioselective Lewis acid-Lewis base bifunctional catalyst
Autore:
Kanai, M; Hamashima, Y; Takamura, M; Shibasaki, M;
Indirizzi:
Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan Univ Tokyo Tokyo Japan 1130033 ceut Sci, Bunkyo Ku, Tokyo 1130033, Japan
Titolo Testata:
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN
fascicolo: 8, volume: 59, anno: 2001,
pagine: 766 - 778
SICI:
0037-9980(200108)59:8<766:DAAOEL>2.0.ZU;2-K
Fonte:
ISI
Lingua:
JPN
Soggetto:
MULTIFUNCTIONAL ASYMMETRIC CATALYSIS; STRECKER-TYPE REACTION; ALPHA-AMINO NITRILES; TRIMETHYLSILYL CYANIDE; CARBONYL-COMPOUNDS; HETEROBIMETALLIC COMPLEXES; ZIRCONIUM CATALYST; MICHAEL ADDITIONS; HYDROGEN-CYANIDE; ALDOL REACTIONS;
Keywords:
bifunctional catalyst; enantioselective reactions; Lewis acid; Lewis base; cyanosilylation; Strecker-type reaction; Reissert-type reaction; epothilones; NMDA-receptor antagonist; chiral quaternary center;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
69
Recensione:
Indirizzi per estratti:
Indirizzo: Kanai, M Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, 7-3-1 Hongo, Tokyo 1130033, Japan Univ Tokyo 7-3-1 Hongo Tokyo Japan 1130033 Tokyo 1130033, Japan
Citazione:
M. Kanai et al., "Development and application of enantioselective Lewis acid-Lewis base bifunctional catalyst", J SYN ORG J, 59(8), 2001, pp. 766-778

Abstract

The design, synthesis, and application of a new bifunctional enantioselective catalyst, containing both Lewis acidity and Lewis basicity, are described. The catalysts are composed of a Lewis acid metal (aluminum or titanium)and a Lewis base (the oxygen atom of a phosphine oxide), of which positions are defined by BINOL or carbohydrate scaffold. Utilizing these catalysts,we have developed a variety of enantio selective cyanation reactions, suchas cyanosilylation of aldehydes and ketones, Strecker-type reaction, and Reissert-type reaction. These reactions showed a broad substrate generality. Investigations toward elucidation of the reaction mechanism, involving kinetic studies. comparison with results by control catalysts, and absolute configurations of the products, revealed that these reactions are catalyzed by a dual activation of a substrate and TMSCN by the Lewis acid and the Lewis base of these catalysts. Catalytic enantioselective total synthesis of anticancer epothilones and a potent NMDA receptor antagonist was achieved, using these reactions as key steps.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 22/01/20 alle ore 13:17:15