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

Date

2014-10-01

Author

Gümüş, Ayşegül
Mert, Kudret
Tanyeli, Cihangir

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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.

Subject Keywords

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

URI

https://hdl.handle.net/11511/35373

Journal

HELVETICA CHIMICA ACTA

DOI

https://doi.org/10.1002/hlca.201300441

Collections

Department of Chemistry, Article

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Citation Formats

A. Gümüş, K. Mert, and C. Tanyeli, “Stereoselective Synthesis of 1,2,3-Triazolooxazine and Fused 1,2,3-Triazolo-delta-Lactone Derivatives,” HELVETICA CHIMICA ACTA, pp. 1340–1344, 2014, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/35373.