Organocatalytic enantioselective Michael addition reactions of fluoromalonates with α,β-unsaturated aldehydes

被引：8

作者：

Li Hao ^{[1
]}

Ji YaFei ^{[2
]}

Li Jian ^{[2
]}

Zhang ShiLei ^{[1
]}

Yu ChenGuang ^{[1
]}

Wang Wei ^{[1
,2
]}

机构：

[1] Univ New Mexico, Dept Chem & Chem Biol, Albuquerque, NM 87131 USA

[2] E China Univ Sci & Technol, Sch Pharm, Dept Pharmaceut Sci, Shanghai 200237, Peoples R China

来源：

SCIENCE CHINA-CHEMISTRY | 2010年 / 53卷 / 01期

关键词：

organocatalysis; alpha; beta-unsaturated aldehydes; chiral fluorinated compounds; Michael addition; CARBONYL-COMPOUNDS; ASYMMETRIC FLUORINATION; ALPHA-FLUOROKETONES; CONJUGATE ADDITION; CINCHONA ALKALOIDS; BETA-KETOESTERS; CATALYSIS; STRATEGIES; ETHERS; HALOGENATION;

D O I：

10.1007/s11426-010-0031-1

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new organocatalytic enantioselective Michael addition of alpha-fluoromalonate to enals has been developed. The process is efficiently catalyzed by readily available chiral diphenylpyrolinol TES ether under mild reaction conditions to afford versatile highly enantioenriched fluorinated aldehydes.

引用

页码：135 / 139

页数：5

共 46 条

[1] Formal Highly Enantioselective Organocatalytic Addition of Fluoromethyl Anion to α,β-Unsaturated Aldehydes
Alba, Andrea-Nekane
Companyo, Xavier
Moyano, Albert
Rios, Ramon
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (29) : 7035 - 7038
[2] Asymmetric alkylation reaction of α-fluorotetralone under phase-transfer catalyzed conditions
Arai, S
Oku, M
Ishida, T
Shioiri, T
[J]. TETRAHEDRON LETTERS, 1999, 40 (37) : 6785 - 6789
[3] Catalytic asymmetric fluorinations
Bobbio, Carla
Gouverneur, Veronique
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (11) : 2065 - 2075
[4] Catalytic asymmetric fluorination comes of age
Brunet, Vincent A.
O'Hagan, David
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (07) : 1179 - 1182
[5] Catalytic asymmetric synthesis of cyclic α-allylated α-fluoroketones
Burger, E. C.
Barron, B. R.
Tunge, J. A.
[J]. SYNLETT, 2006, (17) : 2824 - 2826
[6] Highly enantioselective fluoromalonate addition to α,β-unsaturated aldehydes
Companyo, Xavier
Hejnova, Monika
Kamlar, Martin
Vesely, Jan
Moyano, Albert
Rios, Ramon
[J]. TETRAHEDRON LETTERS, 2009, 50 (35) : 5021 - 5024
[7] Catalytic Enantioselective Michael Addition of 1-Fluoro-bis(phenylsulfonyl)methane to α,β-Unsaturated Ketones Catalyzed by Cinchona Alkaloids
Furukawa, Tatsuya
Shibata, Norio
Mizuta, Satoshi
Nakamura, Shuichi
Toru, Takeshi
Shiro, Motoo
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (42) : 8051 - 8054
[8] Catalytic enantioselective fluorination of oxindoles
Hamashima, Y
Suzuki, T
Takano, H
Shimura, Y
Sodeoka, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (29) : 10164 - 10165
[9] An efficient enantioselective fluorination of various β-ketoesters catalyzed chiral palladium complexes
Hamashima, Y
Yagi, K
Takano, H
Tamás, L
Sodeoka, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (49) : 14530 - 14531
[10] Asymmetric generation of fluorine-containing quaternary carbons adjacent to tertiary stereocenters: uses of fluorinated methines as nucleophiles
Han, Xiao
Luo, Jie
Liu, Chen
Lu, Yixin
[J]. CHEMICAL COMMUNICATIONS, 2009, (15) : 2044 - 2046

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