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...
Published in: | European Journal of Organic Chemistry |
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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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crwiley:10.1002/ejoc.201500760 2024-06-02T07:58:24+00:00 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 Xu, Fan Wu, Qiongsi Chen, Xiaoyang Lin, Xianfu Wu, Qi 2015 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 en eng Wiley http://onlinelibrary.wiley.com/termsAndConditions#vor European Journal of Organic Chemistry volume 2015, issue 24, page 5393-5401 ISSN 1434-193X 1099-0690 journal-article 2015 crwiley https://doi.org/10.1002/ejoc.201500760 2024-05-03T10:41:47Z 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. Article in Journal/Newspaper Antarc* Antarctica Wiley Online Library European Journal of Organic Chemistry 2015 24 5393 5401 |
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Wiley Online Library |
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crwiley |
language |
English |
description |
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. |
format |
Article in Journal/Newspaper |
author |
Xu, Fan Wu, Qiongsi Chen, Xiaoyang Lin, Xianfu Wu, Qi |
spellingShingle |
Xu, Fan Wu, Qiongsi Chen, Xiaoyang Lin, Xianfu Wu, Qi 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 |
author_facet |
Xu, Fan Wu, Qiongsi Chen, Xiaoyang Lin, Xianfu Wu, Qi |
author_sort |
Xu, Fan |
title |
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 |
title_short |
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 |
title_full |
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 |
title_fullStr |
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 |
title_full_unstemmed |
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 |
title_sort |
single lipase‐catalysed one‐pot protocol combining aminolysis resolution and aza‐michael addition: an easy and efficient way to synthesise β‐amino acid esters |
publisher |
Wiley |
publishDate |
2015 |
url |
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 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
European Journal of Organic Chemistry volume 2015, issue 24, page 5393-5401 ISSN 1434-193X 1099-0690 |
op_rights |
http://onlinelibrary.wiley.com/termsAndConditions#vor |
op_doi |
https://doi.org/10.1002/ejoc.201500760 |
container_title |
European Journal of Organic Chemistry |
container_volume |
2015 |
container_issue |
24 |
container_start_page |
5393 |
op_container_end_page |
5401 |
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1800741722149355520 |