Stereoselective Synthesis of 1,2,3‐Triazolooxazine and Fused 1,2,3‐Triazolo‐δ‐Lactone Derivatives |
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| Authors: | Ay?egül Gümü? Kudret Mert Cihangir Tanyeli |
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| Institution: | 1. Department of Chemistry, Faculty of Sciences, Yüzüncü Y?l University, TR‐65080 Van, (phone: +90‐432‐2251024/2248);2. Department of Chemistry, Middle East Technical University, TR‐06800, Ankara |
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| Abstract: | The stereoselective synthesis of 1,2,3‐triazolooxazine and fused 1,2,3‐triazolo‐δ‐lactone by applying chemoenzymatic methods is described. trans‐2‐Azidocyclohexanol was successfully resolved by Novozyme 435 with an ee value of 99%. Installation of the alkyne moiety on the enantiomerically enriched azidoalcohol by O‐alkylation, followed by intramolecular azide? alkyne 3+2] cycloaddition resulted in the desired 1,2,3‐triazolooxazine derivative. Enantiomerically pure azidocyclohexanol was also subjected to the Huisgen 1,3‐dipolar cycloaddition reaction with dimethylacetylene dicarboxylate, followed by intramolecular cyclization of the corresponding cycloadduct, to furnish a fused 1,2,3‐triazolo‐δ‐lactone. |
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| Keywords: | 1 2 3‐Triazolooxazine 1 2 3‐Triazolo‐δ ‐lactone Cyclohexanol 2‐azido‐ Azide alkyne cycloaddition Cycloadditions Enzymatic resolution |
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