title: Facile synthesis and stereo-resolution of chiral 1,2,3-triazoles.
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.
authors: Department of Organic Chemistry, College of Chemistry, Jilin University, No. 2519 Jiefang Road, Changchun 130021, P. R. China. szg@jlu.edu.cn.
authors: Ye
authors: Y
authors: Shi
authors: Xiaohan
authors: X
authors: Ye
authors: Qiang
authors: Q
authors: Gu
authors: Xiaodong
authors: X
authors: Shi
authors: Zhiguang
authors: Z
authors: Song
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry; D003510:Cyclohexanes / Q000737:chemistry; D006900:Hydroxylation; D007700:Kinetics; D008024:Ligands; D009942:Organometallic Compounds / Q000737:chemistry; D013237:Stereoisomerism; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D000475:Alkenes; D003510:Cyclohexanes; D008024:Ligands; D009942:Organometallic Compounds; D014230:Triazoles; C454811:diethylzinc