A chiral triaminosulfonium salt: design and application to catalytic asymmetric synthesis

被引：53

作者：

Kuroki, Y ^{[1
]}

Iseki, K ^{[1
]}

机构：

[1] Daikin Ind Ltd, MEC Lab, Tsukuba, Ibaraki 3050841, Japan

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 47期

关键词：

asymmetric synthesis; catalysts; fluorine; fluorine compounds; sulfonium salts;

D O I：

10.1016/S0040-4039(99)01724-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first chiral triaminosulfonium salt, tris((S,S)-3,4-diphenylpyrrolidino)sulfonium difluorotriphenylstannate, catalyzes trifluoromethylation of benzaldehyde with (trifluoromethyl)trimethylsilane to give the corresponding optically active alcohol with 52% ee. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：8231 / 8234

页数：4

共 10 条

[1] HIGHLY STEREOSELECTIVE REDUCTION OF ALPHA-SUBSTITUTED BETA-KETO AMIDES BY MEANS OF HYDROSILANE/F-AND HYDROSILANE/H+ REAGENT - A PRACTICAL APPROACH TO ALDOLS OF BOTH THREO AND ERYTHRO CONFIGURATIONS [J].

FUJITA, M ;

HIYAMA, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (26) :8294-8296

[2] TETRABUTYLAMMONIUM DIFLUOROTRIPHENYLSTANNATE AS A NEW ANHYDROUS SYNTHETIC EQUIVALENT TO TBAF [J].

GINGRAS, M .

TETRAHEDRON LETTERS, 1991, 32 (50) :7381-7384

[3] GAMMA-SELECTIVE CROSS-COUPLING REACTION OF ALLYLTRIFLUOROSILANES - A NEW APPROACH TO REGIOCHEMICAL CONTROL IN ALLYLIC SYSTEMS [J].

HATANAKA, Y ;

EBINA, Y ;

HIYAMA, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (18) :7075-7076

[4] ASYMMETRIC TRIFLUOROMETHYLATION OF ALDEHYDES AND KETONES WITH TRIFLUOROMETHYLTRIMETHYSILANE CATALYZED BY CHIRAL QUATERNARY AMMONIUM FLUORIDES [J].

ISEKI, K ;

NAGAI, T ;

KOBAYASHI, Y .

TETRAHEDRON LETTERS, 1994, 35 (19) :3137-3138

[5]

Middleton W. J., 1986, Org. Synth, V64, P221, DOI DOI 10.15777/ORGSN.064.0721

[6] SYNTHESES OF DIAZA-SULFONIUM, AZAOXA-SULFONIUM, DIAZAOXA-SULFONIUM, AND TRIAZASULFONIUM IONS [J].

MINATO, H ;

OKUMA, K ;

KOBAYASHI, M .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (04) :652-658

[7] DESIGN AND SYNTHESIS OF NOVEL CHIRAL PYRROLIDINE-BASED DIAMINES WITH C(2)-SYMMETRY [J].

NAKAJIMA, M ;

TOMIOKA, K ;

KOGA, K .

TETRAHEDRON, 1993, 49 (43) :9735-9750

[8] ERYTHRO-SELECTIVE ALDOL REACTION VIA TRIS(DIALKYLAMINO)SULFONIUM ENOLATES [J].

NOYORI, R ;

NISHIDA, I ;

SAKATA, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (08) :2106-2108

[9] NUCLEAR MAGNETIC-RESONANCE DETERMINATION OF ENANTIOMERIC COMPOSITION AND ABSOLUTE-CONFIGURATION OF GAMMA-LACTONES USING CHIRAL 2,2,2-TRIFLUORO-1-(9-ANTHRYL)ETHANOL [J].

PIRKLE, WH ;

SIKKENGA, DL ;

PAVLIN, MS .

JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (02) :384-387

[10] ADDITION OF KETENE TRIMETHYLSILYL ACETALS TO ALPHA,BETA-UNSATURATED KETONES - A NEW STRATEGY FOR MICHAEL ADDITION OF ESTER ENOLATES [J].

RAJANBABU, TV .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (12) :2083-2089

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