Tris(pentafluorophenyl)silyl enol ethers: synthesis and aldol reactions

被引：14

作者：

Dilman, AD

Belyakov, PA

Korlyukov, AA

Tartakovsky, VA

机构：

[1] ND Zelinskii Inst Organ Chem, Moscow 119991, Russia

[2] AN Nesmeyanov Organoelement Cpds Inst, Moscow 119991, Russia

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 19期

基金：

俄罗斯基础研究基金会;

关键词：

silyl enol ethers; silicon Lewis acidity; aldol reaction;

D O I：

10.1016/j.tetlet.2004.03.090

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Silyl enol ethers bearing three pentafluorophenyl groups at the silicon atom are described. These Compounds undergo uncatalyzed aldol reactions with aliphatic, alpha,beta-unsaturated, and aromatic aldehydes. The observed reactivity is analyzed in terms of the Lewis acidity of the silyl fragment. (C) 2004 Elsevier Ltd. All rights reserved.

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收藏

页码：3741 / 3744

页数：4

相关论文

共 25 条

[1] TABLES OF BOND LENGTHS DETERMINED BY X-RAY AND NEUTRON-DIFFRACTION .1. BOND LENGTHS IN ORGANIC-COMPOUNDS [J].

ALLEN, FH ;

KENNARD, O ;

WATSON, DG ;

BRAMMER, L ;

ORPEN, AG ;

TAYLOR, R .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1987, (12) :S1-S19

[2]

BROWNBRIDGE P, 1983, SYNTHESIS-STUTTGART, P85

[3] Determination of the nucleophilicities of silyl and alkyl enol ethers [J].

Burfeindt, J ;

Patz, M ;

Müller, M ;

Mayr, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (15) :3629-3634

[4] ON THE NUCLEOPHILIC ACTIVATION OF SILYL ENOL ETHERS AND ESTERS - A SURVEY AND MECHANISTIC INTERPRETATION [J].

CHUIT, C ;

CORRIU, RJP ;

REYE, C .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1988, 358 (1-3) :57-66

[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] Synthesis and catalytic antibody functionalization of dendrimers [J].

Córdova, A ;

Janda, KD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (34) :8248-8259

[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] CHEMISTRY OF ENOXYSILACYCLOBUTANES - HIGHLY SELECTIVE UNCATALYZED ALDOL ADDITIONS [J].

DENMARK, SE ;

GRIEDEL, BD ;

COE, DM ;

SCHNUTE, ME .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (16) :7026-7043

[9] Asymmetric aldol additions catalyzed by chiral phosphoramides: Electronic effects of the aldehyde component [J].

Denmark, SE ;

Stavenger, RA ;

Wong, KT .

TETRAHEDRON, 1998, 54 (35) :10389-10402

[10] Asymmetric catalysis of aldol reactions with chiral Lewis bases [J].

Denmark, SE ;

Stavenger, RA .

ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) :432-440