Organocatalysis with azahelicenes: the first use of helically chiral pyridine-based catalysts in the asymmetric acyl transfer reaction

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Title:Organocatalysis with azahelicenes: the first use of helically chiral pyridine-based catalysts in the asymmetric acyl transfer reaction
Creators:
Šámal, Michal
Míšek, Jiří
Stará, Irena G.
Starý, Ivo
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 74, 7-8, pp. 1151-1159
Uncontrolled Keywords:Acyl transfer, Asymmetric catalysis, Kinetic resolution, Organocatalysis, Azahelicenes

Abstract

The successful utilisation of a helicene-based organocatalyst in acylative kinetic resolution of racemic secondary alcohol was described. Employing <i>rac</i>-1-phenylethanol, optically pure (–)-(<i>M</i>)-2-aza[6]helicene (5–20 mole %), isobutyric anhydride and <i>N</i>-ethyldiisopropylamine in chloroform at 22–40 °C, an asymmetric acyl transfer reaction took place overwhelming the uncatalysed background process. Moderate reactivity as well as selectivity factor (<i>s</i> = 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.

Title:Organocatalysis with azahelicenes: the first use of helically chiral pyridine-based catalysts in the asymmetric acyl transfer reaction
Creators:
Šámal, Michal
Míšek, Jiří
Stará, Irena G.
Starý, Ivo
Uncontrolled Keywords:Acyl transfer, Asymmetric catalysis, Kinetic resolution, Organocatalysis, Azahelicenes
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:74
Number:7-8
Page Range:pp. 1151-1159
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc2009067UNSPECIFIED
ID Code:4527
Item Type:Article
Deposited On:01 Sep 2009 12:41
Last Modified:01 Sep 2009 10:41

Citation

Šámal, Michal; Míšek, Jiří; Stará, Irena G.; Starý, Ivo (2009) Organocatalysis with azahelicenes: the first use of helically chiral pyridine-based catalysts in the asymmetric acyl transfer reaction. Collection of Czechoslovak Chemical Communications, 74 (7-8). pp. 1151-1159. ISSN 0010-0765

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