An efficient enantioselective synthesis of florfenicol via a vanadium-catalyzed asymmetric epoxidation

作者:Li, Feng; Wang, Zhong-Hua; Zhao, Lei; Xiong, Fang-Jun; He, Qiu-Qin; Chen, Fen-Er*
来源:Tetrahedron: Asymmetry , 2011, 22(12): 1337-1341.
DOI:10.1016/j.tetasy.2011.07.011

摘要

An efficient and highly enantioselective synthesis of florfenicol 1 was achieved with 37% overall yield starting from commercially available 4-methylthiobenzaldehyde. A key feature of the synthesis is the vanadium-catalyzed asymmetric epoxidation of allylic alcohol 5 with aq tert-butyl hydroperoxide to form (2S,3S)-epoxide 6.