Facile synthesis and stereo-resolution of chiral 1,2,3-triazoles
1Department of Organic Chemistry, College of Chemistry, Jilin University, No. 2519 Jiefang Road, Changchun 130021, P. R. China. szg@jlu.edu.cn.
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.
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