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

Molecules

Han Xiao¹  Fang Wu¹  Li Shi¹  Zhiwei Chen¹  Shihu Su¹  Chenghao Tang¹  Hongtao Wang¹  Zhining Li¹  Meichuan Li¹ 

[1] Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang 550025, China; E-Mails:

关键词: β-amino acid ester;    antifungal activity;    benzoheterocycle;    enantioselective synthesis;   

DOI  :  10.3390/molecules19043955

来源: mdpi

【 摘 要 】

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%.

【 授权许可】

CC BY   
© 2014 by the authors; licensee MDPI, Basel, Switzerland.