Catalytic Enantioselective Michael Addition of 1-Fluoro-bis(phenylsulfonyl)methane to α,β-Unsaturated Ketones Catalyzed by Cinchona Alkaloids

被引：124

作者：

Furukawa, Tatsuya ^{[1
]}

Shibata, Norio ^{[1
]}

Mizuta, Satoshi ^{[1
]}

Nakamura, Shuichi ^{[1
]}

Toru, Takeshi ^{[1
]}

Shiro, Motoo ^{[2
]}

机构：

[1] Nagoya Inst Technol, Dept Frontier Mat, Grad Sch Engn, Showa Ku, Nagoya, Aichi 4668555, Japan

[2] Rigaku Corp, Tokyo 1968666, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 42期

关键词：

asymmetric catalysis; cinchona alkaloids; fluorine; Michael addition;

D O I：

10.1002/anie.200802904

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) A catalyst worth its salt: The ammonium salts of cinchona alkaloids possessing sterically demanding substituents effectively catalyzed the enantioselective 1,4-conjugate addition of 1-fluorobis(phenyl- sulfonyl) methane to α,β-unsaturated ketones to furnish the Michael adducts in high yield with excellent enantioselectivity (see scheme). The adducts are useful for the synthesis of chiral monofluoromethylated molecules. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：8051 / 8054

页数：4

共 64 条

[1]

Banks R. E., 1994, ORGANOFLUORINE CHEM

[2] ALPHA-(FLUOROMETHYL)DEHYDROORNITHINE AND ALPHA-(FLUOROMETHYL)DEHYDROPUTRESCINE ANALOGS AS IRREVERSIBLE INHIBITORS OF ORNITHINE DECARBOXYLASE [J].

BEY, P ;

GERHART, F ;

VANDORSSELAER, V ;

DANZIN, C .

JOURNAL OF MEDICINAL CHEMISTRY, 1983, 26 (11) :1551-1556

[3] How to reach stereogenic trifluoromethylated carbon? En route to the "grail" of the asymmetric trifluoromethylation reaction [J].

Billard, Thierry ;

Langlois, Bernard R. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (06) :891-897

[4] Catalytic asymmetric fluorinations [J].

Bobbio, Carla ;

Gouverneur, Veronique .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (11) :2065-2075

[5]

Brunet V.A., 2008, ANGEW CHEM, V120, P1198

[6] Catalytic asymmetric fluorination comes of age [J].

Brunet, Vincent A. ;

O'Hagan, David .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (07) :1179-1182

[7] Enantioselective introduction of fluoride into organic compounds First asymmetric ring opening of epoxides by hydrofluorinating reagents [J].

Bruns, S ;

Haufe, G .

JOURNAL OF FLUORINE CHEMISTRY, 2000, 104 (02) :247-254

[8] Conformational behavior of cinchonidine in different solvents:: A combined NMR and ab initio investigation [J].

Bürgi, T ;

Baiker, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (49) :12920-12926

[9] CONFORMATIONAL STUDY OF CINCHONA ALKALOIDS - A COMBINED NMR, MOLECULAR MECHANICS, AND X-RAY APPROACH [J].

DIJKSTRA, GDH ;

KELLOGG, RM ;

WYNBERG, H ;

SVENDSEN, JS ;

MARKO, I ;

SHARPLESS, KB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (21) :8069-8076

[10]

DIJKSTRA GDH, 1989, RECL TRAV CHIM PAY B, V108, P195

← 1 2 3 4 5 6 7 →