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

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

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 (CC BY 3.0).

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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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