Lewis acid promoted aldol reaction of fluorinated silyl enol ethers from new fluoroacetylsilane derivatives

被引：16

作者：

Chung, WJ ^{[1
]}

Ngo, SC ^{[1
]}

Higashiya, S ^{[1
]}

Welch, JT ^{[1
]}

机构：

[1] SUNY Albany, Dept Chem, Albany, NY 12222 USA

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 28期

基金：

美国国家卫生研究院;

关键词：

fluorinated ketone; Aldol reaction; Lewis acid; fluorinated silyl enol ether;

D O I：

10.1016/j.tetlet.2004.05.055

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New fluorinated silyl enol ethers with various trialkylsilyl groups were synthesized. Various fluorinated beta-hydroxy ketones were synthesized by Lewis acid promoted aldol reaction of silyl enol ethers with diverse aldehydes. Reactivity of various trialkylsilyloxy groups toward Lewis acid was also studied. (C) 2004 Elsevier Ltd. All rights reserved.

引用

收藏

页码：5403 / 5406

页数：4

相关论文

共 19 条

[1] GENERAL-SYNTHESIS OF POLYFUNCTIONALIZED FLUOROMETHYLENEKETONE RETROAMIDES AS POTENTIAL INHIBITORS OF THROMBIN [J].

ALTENBURGER, JM ;

SCHIRLIN, D .

TETRAHEDRON LETTERS, 1991, 32 (49) :7255-7258

[2] Mg0-promoted selective C-F bond cleavage of trifluoromethyl ketones:: a convenient method for the synthesis of 2,2-difluoro enol silanes [J].

Amii, H ;

Kobayashi, T ;

Hatamoto, Y ;

Uneyama, K .

CHEMICAL COMMUNICATIONS, 1999, (14) :1323-1324

[3]

[Anonymous], 1991, Fluorine in Bioorganic Chemistry

[4]

[Anonymous], 1994, Org. React

[5]

BEDNARSKI MD, 1991, COMPREHENSIVE ORGANI, V2

[6] SYNTHESIS OF DIFLUOROENOXYSILANES FROM ACYLSILANES AND TRIFLUOROMETHYLTRIMETHYLSILANE (TFMTMS) - DRAMATIC EFFECT OF THE CATALYTIC FLUORIDE SOURCE [J].

BRIGAUD, T ;

DOUSSOT, P ;

PORTELLA, C .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (18) :2117-2118

[7]

HIGASHIYA S, 2001, 222 NAT M AM CHEM SO

[8] Asymmetric aldol addition of aldehydes to a difluoroketene silyl acetal catalyzed by chiral Lewis acids [J].

Iseki, K ;

Kuroki, Y ;

Asada, D ;

Takahashi, M ;

Kishimoto, S ;

Kobayashi, Y .

TETRAHEDRON, 1997, 53 (30) :10271-10280

[9] 1,1-DIFLUORO-2-TRIPHENYLSILOXYBUTA-1,3-DIENE AS A POTENTIALLY USEFUL FLUORINE-CONTAINING BUILDING BLOCK - PREPARATION AND [4+2] AND [2+2] CYCLOADDITIONS [J].

JIN, FQ ;

XU, YY ;

HUANG, WY .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (10) :814-818

[10] 2,2-DIFLUORO ENOL SILYL ETHERS - CONVENIENT PREPARATION AND APPLICATION TO THE SYNTHESIS OF A NOVEL FLUORINATED BRASSINOSTEROID [J].

JIN, FQ ;

XU, YY ;

HUANG, WY .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (07) :795-799