One-pot synthesis of novel chiral β-amino acid derivatives by enantioselective Mannich reactions catalyzed by squaramide cinchona alkaloids

• Published in: Molecules (Basel, Switzerland) Vol. 18; no. 6; pp. 6142 - 6152
• Main Authors: Zhang, Kankan, Liang, Xueping, He, Ming, Wu, Jian, Zhang, Yuping, Xue, Wei, Jin, Linhong, Yang, Song, Hu, Deyu
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI 23.05.2013; MDPI AG
• Subjects: 1,3,4-thiadiazole moiety; Amino Acids - chemical synthesis; Amino Acids - chemistry; Asymmetric Mannich addition; Catalysis; Chemistry Techniques, Synthetic; Cinchona Alkaloids - chemistry; Molecular Structure; thiourea derived from squaramide cinchona alkaloid; β-amino acid derivatives
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules18066142

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.