Synthesis of chiral 4, 5-dihydrothiazol-2-amines and 4, 5-dihydrooxazol-2-amines through an unexpected ring opening reaction of azetidines. Issue 11 (16th March 2016)

• Record Type: Journal Article
• Authors: Zhou, Xin; Xu, Xingyu; Li, Yi; Zhang, Zhanbin; Zheng, Zhi-bing
• Is Part Of: Tetrahedron letters. Volume 57:Issue 11(2016)
• Page Start: 1236
• Page End: 1238
• Publication Date: 2016-03-16
• Subjects: Azetidine -- Isothiocyanate -- Isocyanate -- Dihydrothiazole -- Dihydrooxazole; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.02.011
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: A general and concise new method to the synthesis of chiral 4, 5-dihydrothiazol-2-amines and 4, 5-dihydrooxazol-2-amines has been developed. Chiral 4, 5-dihydrothiazol-2-amines were made from the reaction of chiral 3-amino-4-aryl-azetidines with isothiocyanates via a completely regio- and stereoselective ring opening reaction of azetidines. And chiral 4, 5-dihydrooxazol-2-amines were synthesized by the isomerization of the urea intermediates in the presence of TFA.