Catalytic Enantioselective Trifluoromethylation of Azomethine Imines with Trimethyl(trifluoromethyl)silane

被引:160
作者
Kawai, Hiroyuki [1 ]
Kusuda, Akihiro [1 ]
Nakamura, Shuichi [1 ]
Shiro, Motoo [2 ]
Shibata, Norio [1 ]
机构
[1] Nagoya Inst Technol, Grad Sch Engn, Dept Frontier Mat, Showa Ku, Nagoya, Aichi 4668555, Japan
[2] Rigaku Corp, Tokyo 1968666, Japan
关键词
amines; autocatalysis; fluorine; organocatalysis; trifluoromethylation; NUCLEOPHILIC TRIFLUOROMETHYLATION; ASYMMETRIC TRIFLUOROMETHYLATION; CARBONYL-COMPOUNDS; 1,3-DIPOLAR CYCLOADDITION; STEREOSELECTIVE-SYNTHESIS; VICINAL ETHYLENEDIAMINES; CINCHONA ALKALOIDS; COMBINED NMR; KETONES; ALDEHYDES;
D O I
10.1002/anie.200902457
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
It's a cinch! The title reaction with azomethine imines 1 uses an operationally simple procedure, based on the combination of the bromide salt of cinchona alkaloids (3) and KOH. The procedure is reliable and general. Trifluoromethyl-substituted amines can be accessed by a two-step deprotection of the product (S)-2. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:6324 / 6327
页数:4
相关论文
共 62 条
[11]   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
[12]  
DIJKSTRA GDH, 1989, RECL TRAV CHIM PAY B, V108, P195
[13]  
Furukawa T., 2008, ANGEW CHEM, V120, P8171
[14]   Catalytic Enantioselective Michael Addition of 1-Fluoro-bis(phenylsulfonyl)methane to α,β-Unsaturated Ketones Catalyzed by Cinchona Alkaloids [J].
Furukawa, Tatsuya ;
Shibata, Norio ;
Mizuta, Satoshi ;
Nakamura, Shuichi ;
Toru, Takeshi ;
Shiro, Motoo .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (42) :8051-8054
[15]   Lewis base catalyzed trifluoromethylation of carbonyl compounds with trialkyl(trifluoromethyl)silanes [J].
Hagiwara, T ;
Kobayashi, T ;
Fuchikami, T .
MAIN GROUP CHEMISTRY, 1997, 2 (01) :13-15
[16]   The many roles for fluorine in medicinal chemistry [J].
Hagmann, William K. .
JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (15) :4359-4369
[17]   ASYMMETRIC TRIFLUOROMETHYLATION OF ALDEHYDES AND KETONES WITH TRIFLUOROMETHYLTRIMETHYSILANE CATALYZED BY CHIRAL QUATERNARY AMMONIUM FLUORIDES [J].
ISEKI, K ;
NAGAI, T ;
KOBAYASHI, Y .
TETRAHEDRON LETTERS, 1994, 35 (19) :3137-3138
[18]   Asymmetric 1,3-dipolar cycloaddition reaction of azomethine imines to allyl alcohol [J].
Kato, Tomomitsu ;
Fujinami, Shuhei ;
Ukaji, Yutaka ;
Inomata, Katsuhiko .
CHEMISTRY LETTERS, 2008, 37 (03) :342-343
[19]   Diastereoselective trifluoromethylation of chiral N-(tolylsulfinyl)imines in the presence of Lewis bases [J].
Kawano, Y ;
Mukaiyama, T .
CHEMISTRY LETTERS, 2005, 34 (07) :894-895
[20]   Fluorine in medicinal chemistry: Recent therapeutic applications of fluorinated small molecules [J].
Kirk, Kenneth L. .
JOURNAL OF FLUORINE CHEMISTRY, 2006, 127 (08) :1013-1029