On the Stereoselectivity of the (-)-Dimenthyl Malonate Addition to α,β-Unsaturated Ketones

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Title:On the Stereoselectivity of the (-)-Dimenthyl Malonate Addition to α,β-Unsaturated Ketones
Creators:
Šebo, Ľubomír
Alföldi, Juraj
Rihs, Grety
Toma, Štefan
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 61, 12, pp. 1805-1814
Uncontrolled Keywords:Enones, Michael addition, (-)-Dimenthyl malonate

Abstract

The Michael addition of (-)-dimenthyl malonate to eight α,β-unsaturated ketones has been studied. The ratio of diastereomers was calculated on the basis of the <sup>1</sup>H NMR spectra of the crude reaction products. The diastereomer excess varied from 10 to 50%, depending on the structure of the starting enone. The pure diastereomer produced by addition of (-)-dimenthyl malonate to 2-benzylidene-1,4-indandione was isolated by repeated crystallization. X-ray analysis has shown that the isomer is (-)-dimenthyl (<i>R</i>)-2-[1-(1,3-dioxoindan-2-yl)-1-phenylmethyl]malonate (<strong>5a</strong>). The predominating diastereomers of (-)-dimenthyl(3-ferrocenyl-3-oxophenylpropyl)malonate (<strong>1a</strong>) and (-)-dimenthyl-2-(1-(1,3-dioxo[3]ferrocenophan-2-yl)-1-phenyl malonate (<strong>6a</strong>) were also isolated in pure state by careful crystallization.

Title:On the Stereoselectivity of the (-)-Dimenthyl Malonate Addition to α,β-Unsaturated Ketones
Creators:
Šebo, Ľubomír
Alföldi, Juraj
Rihs, Grety
Toma, Štefan
Uncontrolled Keywords:Enones, Michael addition, (-)-Dimenthyl malonate
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:12
Page Range:pp. 1805-1814
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19961805UNSPECIFIED
ID Code:1088
Item Type:Article
Deposited On:06 Feb 2009 17:06
Last Modified:06 Feb 2009 16:06

Citation

Šebo, Ľubomír; Alföldi, Juraj; Rihs, Grety; Toma, Štefan (1996) On the Stereoselectivity of the (-)-Dimenthyl Malonate Addition to α,β-Unsaturated Ketones. Collection of Czechoslovak Chemical Communications, 61 (12). pp. 1805-1814. ISSN 0010-0765

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