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Molecules 2013, 18(6), 6142-6152; doi:10.3390/molecules18066142

One-Pot Synthesis of Novel Chiral β-Amino Acid Derivatives by Enantioselective Mannich Reactions Catalyzed by Squaramide Cinchona Alkaloids

State Key Laboratory of Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang 550025, China
These authors contributed equally to this work.
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Author to whom correspondence should be addressed.
Received: 1 April 2013 / Revised: 13 May 2013 / Accepted: 16 May 2013 / Published: 23 May 2013
(This article belongs to the Section Organic Synthesis)
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Abstract

An efficient one-pot synthesis of novel β-amino acid derivatives containing a thiadiazole moiety was developed using a chiral squaramide cinchona alkaloid as organocatalyst. The reactions afforded chiral β-amino acid derivatives in moderate yields and with moderate to excellent enantioselectivities. The present study demonstrated for the first time the use of a Mannich reaction catalyzed by a chiral bifunctional organocatalyst for the one-pot synthesis of novel β-amino acid derivatives bearing a 1,3,4-thiadiazole moiety on nitrogen.
Keywords: Asymmetric Mannich addition; β-amino acid derivatives; 1,3,4-thiadiazole moiety; thiourea derived from squaramide cinchona alkaloid Asymmetric Mannich addition; β-amino acid derivatives; 1,3,4-thiadiazole moiety; thiourea derived from squaramide cinchona alkaloid
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

Zhang, K.; Liang, X.; He, M.; Wu, J.; Zhang, Y.; Xue, W.; Jin, L.; Yang, S.; Hu, D. One-Pot Synthesis of Novel Chiral β-Amino Acid Derivatives by Enantioselective Mannich Reactions Catalyzed by Squaramide Cinchona Alkaloids. Molecules 2013, 18, 6142-6152.

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