Sterically Crowded Heterocycles. XIII. An Insight Into the Absolute Stereochemistry of Atropisomeric (Z)-3-(Imidazo[1,2-a]pyridin-3-yl)prop-2-en-1-ones

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Title:Sterically Crowded Heterocycles. XIII. An Insight Into the Absolute Stereochemistry of Atropisomeric (Z)-3-(Imidazo[1,2-a]pyridin-3-yl)prop-2-en-1-ones
Creators:
Pohl, Radek
Sýkora, Jan
Maloň, Petr
Böhm, Stanislav
Kratochvíl, Bohumil
Kuthan, Josef
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 65, 10, pp. 1643-1652
Uncontrolled Keywords:Absolute configuration, Atropisomerism, Imidazo[1,2-<i>a</i>]pyridines, CD spectroscopy, X-Ray analysis, Semiempirical calculations, PM3 method, Racemization barriers, Axial chirality

Abstract

The absolute configuration of the atropisomeric (<i>Z</i>)-3-(5-methyl-2-phenylimidazo[1,2-<i>a</i>]pyridin-3-yl)-1,3-diphenylprop-2-en-1-one was evaluated to be <i>R</i> for the dextrorotatory and <i>S</i> for the laevorotatory enantiomers. The assignment is based on their two-step syntheses <i>via</i> atropodiastereoisomeric carbamates prepared from the corresponding atropodiastereoisomeric alcohols with (<i>R</i>)-(+)-α-phenylethyl isocyanate and by a complete X-ray space analysis of the quaternary triiodide obtained from the (<i>R</i>)-(+)-enantiomer. CD spectra and PM3 calculated heats of formation for selected compounds are discussed in relation to the found molecular configurations. <p>

Title:Sterically Crowded Heterocycles. XIII. An Insight Into the Absolute Stereochemistry of Atropisomeric (Z)-3-(Imidazo[1,2-a]pyridin-3-yl)prop-2-en-1-ones
Creators:
Pohl, Radek
Sýkora, Jan
Maloň, Petr
Böhm, Stanislav
Kratochvíl, Bohumil
Kuthan, Josef
Uncontrolled Keywords:Absolute configuration, Atropisomerism, Imidazo[1,2-<i>a</i>]pyridines, CD spectroscopy, X-Ray analysis, Semiempirical calculations, PM3 method, Racemization barriers, Axial chirality
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:65
Number:10
Page Range:pp. 1643-1652
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20001643UNSPECIFIED
ID Code:1746
Item Type:Article
Deposited On:06 Feb 2009 17:12
Last Modified:06 Feb 2009 16:12

Citation

Pohl, Radek; Sýkora, Jan; Maloň, Petr; Böhm, Stanislav; Kratochvíl, Bohumil; Kuthan, Josef (2000) Sterically Crowded Heterocycles. XIII. An Insight Into the Absolute Stereochemistry of Atropisomeric (Z)-3-(Imidazo[1,2-a]pyridin-3-yl)prop-2-en-1-ones. Collection of Czechoslovak Chemical Communications, 65 (10). pp. 1643-1652. ISSN 0010-0765

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