Cinchona Alkaloid Derivative-Catalyzed Enantioselective Synthesis via a Mannich-Type Reaction and Antifungal Activity of β-Amino Esters Bearing Benzoheterocycle Moieties

作者：Han Xiao, Fang Wu, Li Shi, Zhiwei Chen, Shihu Su, Chenghao Tang, Hongtao Wang, Zhining Li, Meichuan Li, Qingcai Shi · 发表于：Molecules · 年份：2014 · DOI：10.3390/molecules19043955 · 被引用次数：12 · 研究领域：Asymmetric Synthesis and Catalysis、Synthesis of β-Lactam Compounds、Chemical synthesis and alkaloids

An efficient synthesis of highly functionalized chiral β-amino ester derivatives containing benzothiophene and benzothiazole moieties is developed by a Mannich-type reaction using a cinchona alkaloid-derived thiourea catalyst. The desired products were obtained in good yields and high enantioselectivities (~86% yield, >99% ee) using to the optimized reaction conditions. The synthesized compounds were characterized by 1H-NMR, 13C-NMR, IR, and HREI-MS analyses. The bioassays identified that compound 5dr has excellent antifungal activity, with a 60.53% inhibition rate against F. oxysporum, higher than that of the commercial agricultural fungicide hymexazol, whose inhibition rate was 56.12%.