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Issue 19, 2015
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Facile synthesis and stereo-resolution of chiral 1,2,3-triazoles

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Abstract

We describe herein the first facile synthesis of chiral triazoles through side chain functionalization. Readily available C-vinyl triazoles were used as starting materials, followed by sequential epoxidation, rearrangement and reduction to give the corresponding hydroxyl-triazoles. The CalB lipase catalyzed kinetic resolution gave enantiomerically pure (>99% ee) chiral triazoles in excellent yield. These new chiral TAs were also successfully applied as ligands in asymmetric addition of diethylzinc to aldehydes.

Graphical abstract: Facile synthesis and stereo-resolution of chiral 1,2,3-triazoles

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Publication details

The article was received on 11 Mar 2015, accepted on 31 Mar 2015 and first published on 31 Mar 2015


Article type: Paper
DOI: 10.1039/C5OB00479A
Author version available: Download Author version (PDF)
Citation: Org. Biomol. Chem., 2015,13, 5407-5411
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    Facile synthesis and stereo-resolution of chiral 1,2,3-triazoles

    Y. Shi, X. Ye, Q. Gu, X. Shi and Z. Song, Org. Biomol. Chem., 2015, 13, 5407
    DOI: 10.1039/C5OB00479A

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