A convenient method for the synthesis of (Z)-α-fluoroacrylates:: Lewis base-catalyzed carbonyl fluoroolefination using fluoro(trimethylsilyl)ketene ethyl trimethylsilyl acetal

被引：14

作者：

Michida, Makoto ^{[2
]}

Mukaiyama, Teruaki ^{[1
]}

机构：

[1] Kitasato Univ, Ctr Basic Res, Kita Ku, Tokyo 1140003, Japan

[2] Daiichi Sankyo Co Ltd, Proc Technol Res Labs, Edogawa Ku, Tokyo 1348630, Japan

来源：

CHEMISTRY LETTERS | 2008年 / 37卷 / 08期

关键词：

D O I：

10.1246/cl.2008.890

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly useful method is established for the stereoselective synthesis of (Z)-alpha-fluoroacrylates from various aldehydes and fluoro(trimethylsilyl)ketene ethyl trimethylsilyl acetal in the presence of a Lewis base catalyst. The ketene acetal. easily prepared from ethyl fluoroacetate, affords alpha-fluoroacrylates in high yields with excellent Z stereoselectivities under mild conditions.

引用

页码：890 / 891

页数：2

共 8 条

[1] A convenient method for the Lewis base-catalyzed synthesis of α,β-unsaturated carboxylic esters using trimethylsilylketene ethyl trimethylsilyl acetal and carbonyl compounds
Michida, Makoto
Mukaiyama, Teruaki
CHEMISTRY LETTERS, 2008, 37 (07) : 704 - 705
[2] A convenient method for the synthesis of (Z)-α-haloacrylates: Lewis base-catalyzed carbonyl olefination using α-halo-C,O-bis(trimethylsilyl)ketene acetals
Michida, Makoto
Toriumi, Takako
Mukaiyama, Teruaki
TETRAHEDRON LETTERS, 2009, 50 (26) : 3261 - 3262
[3] Lewis base-catalyzed cyanomethylation of carbonyl compounds with (trimethylsilyl)acetonitrile
Kawano, Y
Kaneko, N
Mukaiyama, T
CHEMISTRY LETTERS, 2005, 34 (11) : 1508 - 1509
[4] Lewis base-catalyzed Michael reactions between trimethylsilyl enolate and α,β-unsaturated carbonyl compounds
Nakagawa, T
Fujisawa, H
Nagata, Y
Mukaiyama, T
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2005, 78 (02) : 236 - 246
[5] Lewis base-catalyzed Michael reactions between trimethylsilyl enolate and α,β-unsaturated carbonyl compounds
Nakagawa, Takashi
Fujisawa, Hidehiko
Nagata, Yuzo
Mukaiyama, Teruaki
Bull. Chem. Soc. Jpn., 2 (236-246):
[6] Lewis base catalyzed 1,3-dithiane addition to carbonyl compounds using 2-trimethylsilyl-1,3-dithiane
Michida, Makoto
Mukaiyama, Teruaki
CHEMISTRY LETTERS, 2008, 37 (01) : 26 - 27
[7] Lewis base catalyzed 1,3-dithiane addition to carbonyl and imino compounds using 2-trimethylsilyl-1,3-dithiane
Michida, Makoto
Mukaiyama, Teruaki
CHEMISTRY-AN ASIAN JOURNAL, 2008, 3 (8-9) : 1592 - 1600
[8] A STEREOCONTROLLED SYNTHESIS OF 3-(1'-HYDROXYETHYL)-2-AZETIDINONES THROUGH TRIMETHYLSILYL TRIFLUOROMETHANESULFONATE CATALYZED CONDENSATION OF SILYL KETENE ACETAL DERIVED FROM ETHYL 3-HYDROXYBUTYRATE AND IMINE
GUANTI, G
NARISANO, E
BANFI, L
TETRAHEDRON LETTERS, 1987, 28 (37) : 4335 - 4338

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