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

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...

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Bibliographic Details
Published in:European Journal of Organic Chemistry
Main Authors: Xu, Fan, Wu, Qiongsi, Chen, Xiaoyang, Lin, Xianfu, Wu, Qi
Format: Article in Journal/Newspaper
Language:English
Published: Wiley 2015
Subjects:
Antarc*
Antarctica
Online Access:http://dx.doi.org/10.1002/ejoc.201500760
https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fejoc.201500760
http://onlinelibrary.wiley.com/wol1/doi/10.1002/ejoc.201500760/fullpdf
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Summary: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.

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