Journal
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS
Volume 74, Issue 7-8, Pages 1151-1159Publisher
INST ORGANIC CHEM AND BIOCHEM
DOI: 10.1135/cccc2009067
Keywords
Azahelicenes; Organocatalysis; Asymmetric catalysis; Acyl transfer; Kinetic resolution
Categories
Funding
- Czech Science Foundation [203/07/1664, 203/09/1766]
- Grant Agency of the Academy of Sciences of the Czech Republic [IAA400550916]
- Ministry of Education, Youth and Sports of the Czech Republic [MSM0021620857, LC512]
- Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic [Z4 055 0506]
Ask authors/readers for more resources
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.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available
Share Paper
