Tetrabutylammonium cyanide catalyzed diasteroselective cyanosliylation of chiral α-hydroxyketones

被引：40

作者：

Amurrio, I ^{[1
]}

Córdoba, R ^{[1
]}

Csákÿ, AG ^{[1
]}

Plumet, J ^{[1
]}

机构：

[1] Univ Complutense, Fac Quim, Dept Quim Organ, Madrid 28040, Spain

来源：

TETRAHEDRON | 2004年 / 60卷 / 46期

关键词：

tetrabutylammonium cyanide; alpha-hydroxyketones; alpha; beta-dihydroxynitriles;

D O I：

10.1016/j.tet.2004.07.101

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Tetrabutylammonium cyanide has been used as non-metallic catalyst for the diastereoselective cyanosilylation of alpha-hydroxyketones derived from the chiral pool. This affords alpha-substituted-alpha,beta-dihydroxynitriles with high levels of asymmetric induction. (C) 2004 Published by Elsevier Ltd.

引用

页码：10521 / 10524

页数：4

共 25 条

[1] An improved synthesis of cyanohydrins in the presence of solid LiClO4 under solvent-free conditions [J].

Azizi, N ;

Saidi, MR .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2003, 688 (1-2) :283-285

[2] Chiral vanadyl Schiff base complex anchored on silicas as solid enantioselective catalysts for formation of cyanohydrins: optimization of the asymmetric induction by support modification [J].

Baleizao, C ;

Gigante, B ;

Garcia, H ;

Corma, A .

JOURNAL OF CATALYSIS, 2003, 215 (02) :199-207

[3] Indium tribromide:: a highly effective catalyst for the addition of trimethylsilyl cyanide to α-hetero-substituted ketones [J].

Bandini, M ;

Cozzi, PG ;

Melchiorre, P ;

Umani-Ronchi, A .

TETRAHEDRON LETTERS, 2001, 42 (16) :3041-3043

[4]

Bandini M, 2002, EUR J ORG CHEM, V2002, P3243

[5] REACTIVITY OF PENTACOORDINATE AND HEXACOORDINATE SILICON-COMPOUNDS AND THEIR ROLE AS REACTION INTERMEDIATES [J].

CHUIT, C ;

CORRIU, RJP ;

REYE, C ;

YOUNG, JC .

CHEMICAL REVIEWS, 1993, 93 (04) :1371-1448

[6] Methyltriphenylphosphonium iodide catalyzes the addition of trimethylsilyl cyanide to aldehydes [J].

Córdoba, R ;

Plumet, J .

TETRAHEDRON LETTERS, 2003, 44 (32) :6157-6159

[7] A CONCISE THIAZOLE MEDIATED SYNTHESIS OF L-(-)-RHODINOSE FROM (S)-ETHYL LACTATE - THE THIAZOLE ROUTE TO DEOXYSUGARS [J].

DONDONI, A ;

FANTIN, G ;

FOGAGNOLO, M ;

PEDRINI, P .

TETRAHEDRON, 1989, 45 (16) :5141-5150

[8]

EVANS DA, 1973, TETRAHEDRON LETT, P4929

[9] ADDITION OF TERT-BUTYLDIMETHYLSILYL OR TERT-BUTYLDIPHENYLSILYL CYANIDE TO HINDERED KETONES [J].

GOLINSKI, M ;

BROCK, CP ;

WATT, DS .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (01) :159-164

[10] Cyanohydrins in nature and the laboratory: Biology, preparations, and synthetic applications [J].

Gregory, RJH .

CHEMICAL REVIEWS, 1999, 99 (12) :3649-3682

← 1 2 3 →