Sterically Crowded Heterocycles. VII. Reduction of Some (Z)-1,3-Diphenyl-3-(2-phenylimidazo[1,2-a]pyridin-3-yl)prop-2-en-1-ones as Their Axial Chirality Probe

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Title:Sterically Crowded Heterocycles. VII. Reduction of Some (Z)-1,3-Diphenyl-3-(2-phenylimidazo[1,2-a]pyridin-3-yl)prop-2-en-1-ones as Their Axial Chirality Probe
Creators:
Kubík, Richard
Böhm, Stanislav
Kuthan, Josef
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 61, 7, pp. 1018-1026
Uncontrolled Keywords:Diastereoisomerism, Borohydride reduction, Imidazo[1,2-<i>a</i>]pyridines, Axial chirality

Abstract

Borohydride reduction of titled ketones <strong>1a</strong>-<strong>1g</strong> gave diastereoisomeric mixtures of (<i>Z</i>)-1,3-diphenyl-3-(2-phenylimidazo[1,2-<i>a</i>]pyridin-3-yl)prop-2-en-1-ols <strong>2a</strong>-<strong>2g</strong> and <strong>3a</strong>-<strong>3g</strong> in which the former ones prevailed. Only individual racemic products were obtained after borohydride reduction of (<i>E</i>)-1,3-diphenyl-3-(2-phenylimidazo[1,2-<i>a</i>]pyridin-3-yl)-prop-2-en-1-one <strong>4</strong> to corresponding 1-hydroxy derivative <strong>5</strong> and by conversion of (<i>Z</i>)-1-oxo derivative <strong>1a</strong> to 1,3-diphenyl-3-(2-phenylimidazo[1,2-<i>a</i>]pyridin-3-yl)propan-1-one (<strong>6</strong>) with sodium hydrogenselenide. Diastereoselectivity of the borohydride reduction is discussed using the PM3 calculations of the molecules <strong>1a</strong>, <strong>2a</strong>, <strong>2b</strong>, <strong>3a</strong>, <strong>3b</strong>, <strong>4</strong>, <strong>5</strong>, and <strong>6</strong>.

Title:Sterically Crowded Heterocycles. VII. Reduction of Some (Z)-1,3-Diphenyl-3-(2-phenylimidazo[1,2-a]pyridin-3-yl)prop-2-en-1-ones as Their Axial Chirality Probe
Creators:
Kubík, Richard
Böhm, Stanislav
Kuthan, Josef
Uncontrolled Keywords:Diastereoisomerism, Borohydride reduction, Imidazo[1,2-<i>a</i>]pyridines, 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:61
Number:7
Page Range:pp. 1018-1026
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19961018UNSPECIFIED
ID Code:1005
Item Type:Article
Deposited On:06 Feb 2009 17:05
Last Modified:06 Feb 2009 16:05

Citation

Kubík, Richard; Böhm, Stanislav; Kuthan, Josef (1996) Sterically Crowded Heterocycles. VII. Reduction of Some (Z)-1,3-Diphenyl-3-(2-phenylimidazo[1,2-a]pyridin-3-yl)prop-2-en-1-ones as Their Axial Chirality Probe. Collection of Czechoslovak Chemical Communications, 61 (7). pp. 1018-1026. ISSN 0010-0765

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