Additive effects on ligand activated allylation of aldehydes by allyltrichlorosilane

被引：54

作者：

Short, JD ^{[1
]}

Attenoux, S ^{[1
]}

Berrisford, DJ ^{[1
]}

机构：

[1] UNIV MANCHESTER,INST SCI & TECHNOL,DEPT CHEM,MANCHESTER M60 1QD,LANCS,ENGLAND

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 13期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1016/S0040-4039(97)00312-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The rate of allylation of aldehydes using a combination of allyltrichlorosilane and O-donor ligands can be profoundly accelerated by the addition of a range of simple tetra-n-butylammonium salts. Measured t(1/2) values decrease from over 6 hours under defined conditions to less than 5 minutes in favourable cases. These effects are highly relevant to the development of a catalytic asymmetric variant of this reaction and provide insight into the mechanism. (C) 1997 Elsevier Science Ltd.

引用

页码：2351 / 2354

页数：4

共 25 条

[1] ENANTIOSELECTIVE AND DIASTEREOSELECTIVE CATALYSIS OF ADDITION-REACTION OF ALLYLIC SILANES AND STANNANES TO GLYOXYLATES BY BINAPHTHOL-DERIVED TITANIUM COMPLEX [J].

AOKI, S ;

MIKAMI, K ;

TERADA, M ;

NAKAI, T .

TETRAHEDRON, 1993, 49 (09) :1783-1792

[2] Solvated silylium cations: Structure determination by NMR spectroscopy and the NMR/Ab initio/IGLO method [J].

Arshadi, M ;

Johnels, D ;

Edlund, U ;

Ottosson, CH ;

Cremer, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (21) :5120-5131

[3] CATALYTIC ASYMMETRIC-SYNTHESIS PROMOTED BY A CHIRAL ZIRCONATE - HIGHLY ENANTIOSELECTIVE ALLYLATION OF ALDEHYDES [J].

BEDESCHI, P ;

CASOLARI, S ;

COSTA, AL ;

TAGLIAVINI, E ;

UMANIRONCHI, A .

TETRAHEDRON LETTERS, 1995, 36 (43) :7897-7900

[4] Aspects of remote asymmetric induction using allylstannanes [J].

Carey, JS ;

Coulter, TS ;

Hallett, DJ ;

Maguire, RJ ;

McNeill, AH ;

Stanway, SJ ;

Teerawutgulrag, A ;

Thomas, EJ .

PURE AND APPLIED CHEMISTRY, 1996, 68 (03) :707-710

[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] CATALYTIC ASYMMETRIC-SYNTHESIS OF HOMOALLYLIC ALCOHOLS [J].

COSTA, AL ;

PIAZZA, MG ;

TAGLIAVINI, E ;

TROMBINI, C ;

UMANIRONCHI, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (15) :7001-7002

[7] Chemistry of trichlorosilyl enolates .1. New reagents for catalytic, asymmetric aldol additions [J].

Denmark, SE ;

Winter, SBD ;

Su, XP ;

Wong, KT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (31) :7404-7405

[8] ASYMMETRIC ALLYLATION OF ALDEHYDES WITH CHIRAL LEWIS-BASES [J].

DENMARK, SE ;

COE, DM ;

PRATT, NE ;

GRIEDEL, BD .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (21) :6161-6163

[9] Asymmetric allylation of aldehydes catalyzed by substoichiometric amounts of chiral phosphoramides [J].

Iseki, K ;

Kuroki, Y ;

Takahashi, M ;

Kobayashi, Y .

TETRAHEDRON LETTERS, 1996, 37 (29) :5149-5150

[10] CATALYTIC ASYMMETRIC ALLYLATION USING A CHIRAL (ACYLOXY)BORANE COMPLEX AS A VERSATILE LEWIS-ACID CATALYST [J].

ISHIHARA, K ;

MOURI, M ;

GAO, QZ ;

MARUYAMA, T ;

FURUTA, K ;

YAMAMOTO, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (24) :11490-11495

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