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Synthesis of D-Glucose-based Azacrown Ethers with Phosphinoxidoalkyl Side Chains and Their Application to an Enantioselective Reaction |
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| Authors: | Tibor Novák Péter Bakó György Keglevich András Dobó Károly Vékey László Tóke |
| Institution: | (1) Department Of Organic Chemical Technology, Budapest University Of Technology And Economics, 1521 Budapest, Hungary;(2) Chemical Research Center, Hungarian Academy Of Sciences, 1525 Budapest, Hungary;(3) Research Group of the Hungarian Academy of Sciences at the Department of Organic Chemical Technology, Budapest University of Technology and Economics, 1521 Budapest, Hungary |
| Abstract: | Five chiral  -D-glucose-based monoaza-15-crown-5 ethers with phosphinoxidoalkyl side chains of one to five carbon atoms (5a–e)have been synthesised. The cation binding ability of the new lariat ethers was evaluated bythe picrate extraction method. The substituents at the nitrogen atom were not a major influenceon the cation extraction ability of the azacrown ether; the compounds showed, however, a significant asymmetric induction as phase transfer catalysts in the Michael addition of2-nitropropane to chalcone (95% ee). |
| Keywords: | azacrown ethers chiral lariat ethers monoaza-15-crown-5 phosphinoxidoalkyl side chain enantioselective synthesis extraction ability |
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