A Single Lipase‐Catalysed One‐Pot Protocol Combining Aminolysis Resolution and Aza‐Michael Addition: An Easy and Efficient Way to Synthesise β‐Amino Acid Esters. Issue 24 (17th July 2015)

• Record Type: Journal Article
• Authors: Xu, Fan; Wu, Qiongsi; Chen, Xiaoyang; Lin, Xianfu; Wu, Qi
• Is Part Of: European journal of organic chemistry. Issue 24(2015)
• Page Start: 5393
• Page End: 5401
• Publication Date: 2015-07-17
• Subjects: Synthetic methods -- Michael addition -- Enzyme catalysis -- Amino acids -- Kinetic resolution; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201500760
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A novel one‐pot protocol combining aza‐Michael addition and aminolysis resolution was developed to obtain chiral β‐amino acid esters with lipase B from Candida antarctica (CAL‐B) as the only catalyst. This method is conducted under mild reaction conditions and is very easy to handle. After a series of detailed optimization studies, ten racemic aromatic or aliphatic amines were subjected to this one‐pot procedure, and twelve chiral β‐amino acid esters and ten chiral amides were successfully synthesised with excellent ee values in theoretical yields. Scaled‐up procedures also worked without apparent reduction in reaction rate or enantioselectivity, which makes this method suitable for large‐scale production of chiral β‐amino acid esters. Abstract : A one‐pot protocol for simultaneous synthesis of chiral β‐amino acid esters and amides was developed by combining single lipase B from Candida antarctica (CAL‐B) catalysed aza‐Michael addition and aminolysis resolution. This method requires mild reaction conditions and is very easy to handle. Chiral β‐amino acid esters and chiral amides were obtained with excellent ee values and in theoretical yields.