Stereoselective Synthesis of 1,2,3-Triazolooxazine and Fused 1,2,3-Triazolo-delta-Lactone Derivatives

作者：Gumus Aysegul^*; Mert Kudret; Tanyeli Cihangir

来源：Helvetica Chimica Acta, 2014, 97(10): 1340-1344.

DOI：10.1002/hlca.201300441

• 1
• 2
• 3-Triazolooxazine
• 1
• 2
• 3-Triazolo--lactone
• Cyclohexanol
• 2-azido-
• Azidealkyne cycloaddition
• Cycloadditions
• Enzymatic resolution

The stereoselective synthesis of 1,2,3-triazolooxazine and fused 1,2,3-triazolo--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 azidealkyne [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--lactone.

• 出版日期2014-10