Enantioselective Pd-catalyzed allylation reaction of fluorinated silyl enol ethers

被引：158

作者：

Belanger, Etienne ^{[1
]}

Cantin, Katy ^{[1
]}

Messe, Olivier ^{[1
]}

Tremblay, Melanie ^{[1
]}

Paquin, Jean-Francois ^{[1
]}

机构：

[1] Univ Laval, Canada Res Chair Organ & Med Chem, Dept Chim, Quebec City, PQ G1K 7P4, Canada

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2007年 / 129卷 / 05期

关键词：

D O I：

10.1021/ja067501q

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An enantioselective Pd-catalyzed allylation reaction of fluorinated silyl enol ethers is reported. This reaction provides a stereoselective and efficient approach to allylated tertiary -fluoroketones from achiral fluorinated precursors. A variety of cyclic silyl enol ether can be used, and the yields of the desired products range from 52 to 93%, and the enantiomeric excesses range from 83 to 95% ee.

引用

页码：1034 / 1035

页数：2

共 27 条

[1] The enantioselective Tsuji allylation [J].

Behenna, DC ;

Stoltz, BM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (46) :15044-15045

[2] New developments in stereoselective palladium-catalyzed allylic alkylations of preformed enolates [J].

Braun, M ;

Meier, T .

SYNLETT, 2006, (05) :661-676

[3] Synthesis of polyfluorinated nitrogen-containing heterocycles from hemifluorinated enones or organofluorosilicon building blocks as synthetic equivalents [J].

Chanteau, F ;

Didier, B ;

Dondy, B ;

Doussot, P ;

Plantier-Royon, R ;

Portella, C .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (07) :1444-1454

[4] Chiral fluoro ketones for catalytic asymmetric epoxidation of alkenes with oxone [J].

Denmark, SE ;

Matsuhashi, H .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (10) :3479-3486

[5] Iridium-catalyzed regio- and enantioselective allylation of ketone enolates [J].

Graening, T ;

Hartwig, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (49) :17192-17193

[6] Catalytic enantioselective fluorination of oxindoles [J].

Hamashima, Y ;

Suzuki, T ;

Takano, H ;

Shimura, Y ;

Sodeoka, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (29) :10164-10165

[7] Enantioselective fluorination reactions catalyzed by chiral palladium complexes [J].

Hamashima, Yoshitaka ;

Sodeoka, Mikiko .

SYNLETT, 2006, (10) :1467-1478

[8] A new sequential defluorination route to α-fluoro-α,β-unsaturated ketones from trifluoromethyl ketones [J].

Hata, H ;

Kobayashi, T ;

Amii, H ;

Uneyama, K ;

Welch, JT .

TETRAHEDRON LETTERS, 2002, 43 (35) :6099-6102

[9] Phosphinooxazolines - A new class of versatile, modular P,N-ligands for asymmetric catalysis [J].

Helmchen, G ;

Pfaltz, A .

ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) :336-345

[10]

HIYAMA T, 2000, ORGANOFLUORINE COMPO, P1

← 1 2 3 →