Abstract
The chiral monoaza-15-crown-5 lariat ethers annellated to methyl-4,6-O-benzylidene-α-D-glucopyranoside- (1) or – mannopyranoside (2) used as phase transfer catalysts in the Michael addition of 2-nitropropane to substituted chalcones and chalcone analogues resulted in a significant asymmetric induction. The type of substituent on the chalcone molecule was found to have a significant influence on both the chemical yield and the enantioselectivity of the reaction: 24 novel chiral Michael adducts were prepared in 14-68% ee. These ee values were somewhat lower than that experienced in the case of the unsubstituted chalcone (85% ee). In the series of chalcone analogues, the 1-naphthyl Michael adduct was formed in 87% ee. Using glucose-based crown ether 1, formation of the (+)-enantiomers was preferred, while applying mannose-based 2 as the catalyst, the (-)-enantiomers were in excess.
Keywords: Chiral crown ether, phase transfer catalysis, asymmetric Michael addition
Letters in Organic Chemistry
Title: Enantioselective Michael Addition of 2-Nitropropane to Substituted Chalcones and Chalcone Analogues Catalyzed by Chiral Crown Ethers Incorporating an α-D-Glucose or an α-D-Mannose Unit
Volume: 7 Issue: 6
Author(s): Attila Mako, Zsolt Rapi, Laszlo Drahos, Aron Szollosy, Gyorgy Keglevich and Peter Bako
Affiliation:
Keywords: Chiral crown ether, phase transfer catalysis, asymmetric Michael addition
Abstract: The chiral monoaza-15-crown-5 lariat ethers annellated to methyl-4,6-O-benzylidene-α-D-glucopyranoside- (1) or – mannopyranoside (2) used as phase transfer catalysts in the Michael addition of 2-nitropropane to substituted chalcones and chalcone analogues resulted in a significant asymmetric induction. The type of substituent on the chalcone molecule was found to have a significant influence on both the chemical yield and the enantioselectivity of the reaction: 24 novel chiral Michael adducts were prepared in 14-68% ee. These ee values were somewhat lower than that experienced in the case of the unsubstituted chalcone (85% ee). In the series of chalcone analogues, the 1-naphthyl Michael adduct was formed in 87% ee. Using glucose-based crown ether 1, formation of the (+)-enantiomers was preferred, while applying mannose-based 2 as the catalyst, the (-)-enantiomers were in excess.
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Cite this article as:
Mako Attila, Rapi Zsolt, Drahos Laszlo, Szollosy Aron, Keglevich Gyorgy and Bako Peter, Enantioselective Michael Addition of 2-Nitropropane to Substituted Chalcones and Chalcone Analogues Catalyzed by Chiral Crown Ethers Incorporating an α-D-Glucose or an α-D-Mannose Unit, Letters in Organic Chemistry 2010; 7 (6) . https://dx.doi.org/10.2174/157017810791824865
DOI https://dx.doi.org/10.2174/157017810791824865 |
Print ISSN 1570-1786 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6255 |
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