Chiral 1,2,4-triazoles: stereoselective acylation and chlorination |
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Authors: | Alan R Katritzky Dmytro Fedoseyenko Myong S Kim Peter J Steel |
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Institution: | 1. Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA;2. Department of Chemistry, University of Canterbury, Christchurch, New Zealand |
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Abstract: | Acyl groups are transferred from diverse N- and O-acyl derivatives of chiral 3,5-bis-(1-hydroxyethyl)-1,2,4]-triazole to amino acid esters enantioselectively, with 7% to 68% ee, depending on the temperature conditions and nature of the reagents. Thionyl chloride replaced the hydroxyl groups of (S)-1-4-amino-5-((S)-1-hydroxy-ethyl)-1,2,4]-triazol-3-yl]-ethanol 3 stereospecifically with inversion, as confirmed by X-ray analysis, which also revealed unusual crystal structures with asymmetric units comprising three molecules of 4-amino-3,5-bis(R-1-chloroethyl)-1,2,4-triazole 5 and four of 3,5-bis((R)-1-chloroethyl)-1H-1,2,4-triazole 6. |
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