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

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 34期

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

页码：6324 / 6327

页数：4

共 62 条

[1]

[Anonymous], 2006, ANGEW CHEM

[2]

Bgu J.-P., 2008, Bioorganic and Medicinal Chemistry of Fluorine

[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] 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

[5]

Caron S, 2003, SYNTHESIS-STUTTGART, P1693

[6] Process research and development of an NK-1 receptor antagonist. enantioselective trifluoromethyl addition to a ketone in the preparation of a chiral isochroman [J].

Caron, Stephane ;

Do, Nga M. ;

Sieser, Janice E. ;

Arpin, Patrice ;

Vazquez, Enrique .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2007, 11 (06) :1015-1024

[7]

*CCDC, 738896 CCDC

[8]

Chen W., 2007, ANGEW CHEM, V119, P7811

[9] Enantioselective 1,3-dipolar cycloaddition of cyclic enones catalyzed by multifunctional primary amines: Beneficial effects of hydrogen bonding [J].

Chen, Wei ;

Du, Wei ;

Duan, Yong-Zheng ;

Wu, Yong ;

Yang, Sheng-Yong ;

Chen, Ying-Chun .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (40) :7667-7670

[10] Organocatalytic and stereoselective [3+2] cycloadditions of azomethine imines with α,β-unsaturated aldehydes [J].

Chen, Wei ;

Yuan, Xiang-Hong ;

Li, Rui ;

Du, Wei ;

Wu, Yong ;

Ding, Li-Sheng ;

Chen, Ying-Chun .

ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (14) :1818-1822

← 1 2 3 4 5 6 7 →