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Titolo:
Synthesis of (Rc,Ss)-1,1,1-trifluoro-3-(p-tolylsulfinyl)-2-propanol by an asymmetric reduction with a yeast, Yamadazyma farinosa, as a key-step
Autore:
Sakai, A; Bakke, M; Ohta, H; Kosugi, H; Sugai, T;
Indirizzi:
Keio Univ, Dept Chem, Yokohama, Kanagawa 2238522, Japan Keio Univ Yokohama Kanagawa Japan 2238522 kohama, Kanagawa 2238522, Japan Tohoku Univ, Inst Chem Res, Sendai, Miyagi 9808577, Japan Tohoku Univ Sendai Miyagi Japan 9808577 es, Sendai, Miyagi 9808577, Japan
Titolo Testata:
CHEMISTRY LETTERS
fascicolo: 11, , anno: 1999,
pagine: 1255 - 1256
SICI:
0366-7022(199911):11<1255:SO(BAA>2.0.ZU;2-S
Fonte:
ISI
Lingua:
ENG
Soggetto:
BETA-HYDROXY SULFOXIDES; BAKERS-YEAST; ENANTIOSELECTIVE PROTONATION; SECONDARY ALCOHOLS; KINETIC RESOLUTION; ESTERS; PURIFICATION; ENANTIOMERS; OXIDATION; ACETATES;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
33
Recensione:
Indirizzi per estratti:
Indirizzo: Sugai, T Keio Univ, Dept Chem, 3-14-1 Hiyoshi, Yokohama, Kanagawa 2238522,Japan Keio Univ 3-14-1 Hiyoshi Yokohama Kanagawa Japan 2238522 2, Japan
Citazione:
A. Sakai et al., "Synthesis of (Rc,Ss)-1,1,1-trifluoro-3-(p-tolylsulfinyl)-2-propanol by an asymmetric reduction with a yeast, Yamadazyma farinosa, as a key-step", CHEM LETT, (11), 1999, pp. 1255-1256

Abstract

(Rc,Ss)-1,1,1-trifluoro-3-(p-tolylsulfinyl)-2-propanol (>99% e.e.), an important reagent for the asymmetric protonation of substituted enolates, was prepared (70%) from (S)-methyl p-tolyl sulfoxide. The stereoselectivity of the Yamdazyma farinosa-catalyzed reduction of carbonyl groups, the key stepfor the introduction of an asymmetric carbon, was greatly affected by the stereochemistry of the asymmetric sulfur atom. The reduction of (S)1,1,1-trifluoro-3-(p-tolylsulfinyl)-2-propanone proceeded smoothly and in a quite stereoselective manner to give the desired compound, while a 76:24 mixture of (Rc,Rs)-and (Sc,Rs)-isomers was obtained from the substrate with the opposite (R)-configuration.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 23/09/20 alle ore 21:00:06