Stereoselectivity of Michael Addition to 3-Phenyl-1-(η6-o-tolyltricarbonylchromium)propenone

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Title:Stereoselectivity of Michael Addition to 3-Phenyl-1-(η6-o-tolyltricarbonylchromium)propenone
Creators:
Šebo, Ľubomír
Šraga, Ján
Rihs, Grety
Toma, Štefan
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 59, 12, pp. 2621-2631

Abstract

<p>The stereoselectivity of the Michael addition of several <i>C</i>-nucleophiles to 3-phenyl-1-(η<sup>6</sup>-<i>o</i>-tolyltricarbonylchromium)propenone has been studied. The ratio of diastereoisomers formed varied from 65 : 35 (malonodinitrile), 72 : 28 (methyl cyanoacetate) and 78 : 22 (nitromethane) and to 90 : 10 (dimethyl malonate). The ratio of diastereoisomers 63 : 37 was found even when addition of dimethyl malonate was carried out at 75&nbsp;°C in methanol using piperidine as the catalyst. The (<i>S,R</i>) or (<i>R,S</i>) configuration of the main pair of isomers was proved by the X-ray analysis of the dimethyl malonate adduct.

Title:Stereoselectivity of Michael Addition to 3-Phenyl-1-(η6-o-tolyltricarbonylchromium)propenone
Creators:
Šebo, Ľubomír
Šraga, Ján
Rihs, Grety
Toma, Štefan
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:59
Number:12
Page Range:pp. 2621-2631
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19942621UNSPECIFIED
ID Code:681
Item Type:Article
Deposited On:06 Feb 2009 17:03
Last Modified:06 Feb 2009 16:03

Citation

Šebo, Ľubomír; Šraga, Ján; Rihs, Grety; Toma, Štefan (1994) Stereoselectivity of Michael Addition to 3-Phenyl-1-(η6-o-tolyltricarbonylchromium)propenone. Collection of Czechoslovak Chemical Communications, 59 (12). pp. 2621-2631. ISSN 0010-0765

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