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

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

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Received: 1 April 2013; in revised form: 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 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

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.

AMA 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(6):6142-6152.

Chicago/Turabian Style

Zhang, Kankan; Liang, Xueping; He, Ming; Wu, Jian; Zhang, Yuping; Xue, Wei; Jin, Linhong; Yang, Song; Hu, Deyu. 2013. "One-Pot Synthesis of Novel Chiral β-Amino Acid Derivatives by Enantioselective Mannich Reactions Catalyzed by Squaramide Cinchona Alkaloids." Molecules 18, no. 6: 6142-6152.


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