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Molecules 2014, 19(4), 3955-3972; doi:10.3390/molecules19043955
Article

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

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1 Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang 550025, China 2 School of Chemistry and Environmental Science, Guizhou Minzu University, Guiyang 550025, China
* Author to whom correspondence should be addressed.
Received: 7 March 2014 / Revised: 19 March 2014 / Accepted: 21 March 2014 / Published: 1 April 2014
(This article belongs to the Section Organic Synthesis)
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Abstract

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%.
Keywords: β-amino acid ester; antifungal activity; benzoheterocycle; enantioselective synthesis β-amino acid ester; antifungal activity; benzoheterocycle; enantioselective synthesis
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Xiao, H.; Wu, F.; Shi, L.; Chen, Z.; Su, S.; Tang, C.; Wang, H.; Li, Z.; Li, M.; Shi, Q. Cinchona Alkaloid Derivative-Catalyzed Enantioselective Synthesis via a Mannich-Type Reaction and Antifungal Activity of β-Amino Esters Bearing Benzoheterocycle Moieties. Molecules 2014, 19, 3955-3972.

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