title: Concise and scalable asymmetric synthesis of 5-(1-amino-2,2,2-trifluoroethyl)thiazolo[3,2-b][1,2,4]triazoles.
abstract: This study describes asymmetric Mannich-type additions between C-5 lithiated thiazolo[3,2-b][1,2,4]triazoles and enantiomerically pure (SS)-N-tert-butanesulfinyl-(3,3,3)-trifluoroacetaldimine. Under the optimized conditions, these reactions proceed with good (up to 78%) chemical yields and virtually complete (98 : 2 to >99 : 1 dr) diastereoselectivity. The same stereochemical outcome was obtained using 1.05 g scale of the starting (3,3,3)-trifluoroacetaldimine. The method developed in this work provides concise and generalized access to thiazolo[3,2-b][1,2,4]triazoles containing a chiral (trifluoro)ethylamine group.
authors.affiliation: School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, China. hanjl@nju.edu.cn.
authors.forename: Haibo
authors.initials: H
authors.lastname: Mei
authors.forename: Yiwen
authors.initials: Y
authors.lastname: Xiong
authors.forename: Chen
authors.initials: C
authors.lastname: Xie
authors.forename: Vadim A
authors.initials: VA
authors.lastname: Soloshonok
authors.forename: Jianlin
authors.initials: J
authors.lastname: Han
authors.forename: Yi
authors.initials: Y
authors.lastname: Pan
mesh_terms: D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism; D013844:Thiazoles / Q000138:chemical synthesis* / Q000737:chemistry; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D013844:Thiazoles; D014230:Triazoles