ORGANOCATALYSIS WITH AZAHELICENES: THE FIRST USE OF HELICALLY CHIRAL PYRIDINE-BASED CATALYSTS IN THE ASYMMETRIC ACYL TRANSFER REACTION

被引：45
作者：
Samal, Michal [1 ]
Misek, Jiri [1 ]
Stara, Irena G. [1 ]
Stary, Ivo [1 ,2 ]
机构：
[1] Acad Sci Czech Republic, Inst Organ Chem & Biochem, Ctr Biomol & Complex Mol Syst, CR-16610 Prague 6, Czech Republic
[2] Charles Univ Prague, Dept Organ Chem, Prague 12840 2, Czech Republic
来源：
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS | 2009年 / 74卷 / 7-8期
关键词：
Azahelicenes; Organocatalysis; Asymmetric catalysis; Acyl transfer; Kinetic resolution; KINETIC RESOLUTION; SEC-ALCOHOLS; ACYLATION; 4-DIALKYLAMINOPYRIDINES; 1-AND;
D O I：
10.1135/cccc2009067
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The successful utilisation of a helicene-based organocatalyst in acylative kinetic resolution of racemic secondary alcohol was described. Employing rac-1-phenylethanol, optically pure (-)-(M)-2-aza[6]helicene (5-20 mole %), isobutyric anhydride and N-ethyldiisopropylamine in chloroform at 22-40 degrees C, an asymmetric acyl transfer reaction took place overwhelming the uncatalysed background process. Moderate reactivity as well as selectivity factor (s = 9, 10) were observed. An effective control of the enantiodiscriminating step in acylative kinetic resolution by the helically chiral organocatalyst was proven for the first time.
引用
收藏
页码：1151 / 1159
页数：9
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