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Diastereo‐ and Enantioselective Reductive Mannich‐type Reaction of α,β‐Unsaturated Carboxylic Acids to Ketimines: A Direct Entry to Unprotected β (2,3,3)‐Amino Acids
Stereoselective construction of unprotected β‐amino acids is a significant challenge owing to the lack of methods for the catalytic generation of highly enantioenriched carboxylic acid enolates. In this study, a novel copper‐catalyzed diastereo‐ and enantioselective reductive Mannich‐type reaction o...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10107894/ https://www.ncbi.nlm.nih.gov/pubmed/36341524 http://dx.doi.org/10.1002/chem.202202575 |
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author | Suzuki, Hirotsugu Kondo, Sora Yamada, Koichiro Matsuda, Takanori |
author_facet | Suzuki, Hirotsugu Kondo, Sora Yamada, Koichiro Matsuda, Takanori |
author_sort | Suzuki, Hirotsugu |
collection | PubMed |
description | Stereoselective construction of unprotected β‐amino acids is a significant challenge owing to the lack of methods for the catalytic generation of highly enantioenriched carboxylic acid enolates. In this study, a novel copper‐catalyzed diastereo‐ and enantioselective reductive Mannich‐type reaction of α,β‐unsaturated carboxylic acids was developed, which provides a direct and scalable synthetic method for enantioenriched β (2,3,3)‐amino acids with vicinal stereogenic centers. The protocol features in situ generation of transiently protected carboxylic acids by a hydrosilane and their diastereo‐ and enantioselective reductive coupling with ketimines. The synthetic utility of this process was demonstrated by a gram‐scale reaction and the transformation of β‐amino acids. |
format | Online Article Text |
id | pubmed-10107894 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-101078942023-04-18 Diastereo‐ and Enantioselective Reductive Mannich‐type Reaction of α,β‐Unsaturated Carboxylic Acids to Ketimines: A Direct Entry to Unprotected β (2,3,3)‐Amino Acids Suzuki, Hirotsugu Kondo, Sora Yamada, Koichiro Matsuda, Takanori Chemistry Research Articles Stereoselective construction of unprotected β‐amino acids is a significant challenge owing to the lack of methods for the catalytic generation of highly enantioenriched carboxylic acid enolates. In this study, a novel copper‐catalyzed diastereo‐ and enantioselective reductive Mannich‐type reaction of α,β‐unsaturated carboxylic acids was developed, which provides a direct and scalable synthetic method for enantioenriched β (2,3,3)‐amino acids with vicinal stereogenic centers. The protocol features in situ generation of transiently protected carboxylic acids by a hydrosilane and their diastereo‐ and enantioselective reductive coupling with ketimines. The synthetic utility of this process was demonstrated by a gram‐scale reaction and the transformation of β‐amino acids. John Wiley and Sons Inc. 2022-12-08 2023-01-18 /pmc/articles/PMC10107894/ /pubmed/36341524 http://dx.doi.org/10.1002/chem.202202575 Text en © 2022 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH https://creativecommons.org/licenses/by-nc/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc/4.0/ (https://creativecommons.org/licenses/by-nc/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes. |
spellingShingle | Research Articles Suzuki, Hirotsugu Kondo, Sora Yamada, Koichiro Matsuda, Takanori Diastereo‐ and Enantioselective Reductive Mannich‐type Reaction of α,β‐Unsaturated Carboxylic Acids to Ketimines: A Direct Entry to Unprotected β (2,3,3)‐Amino Acids |
title | Diastereo‐ and Enantioselective Reductive Mannich‐type Reaction of α,β‐Unsaturated Carboxylic Acids to Ketimines: A Direct Entry to Unprotected β
(2,3,3)‐Amino Acids |
title_full | Diastereo‐ and Enantioselective Reductive Mannich‐type Reaction of α,β‐Unsaturated Carboxylic Acids to Ketimines: A Direct Entry to Unprotected β
(2,3,3)‐Amino Acids |
title_fullStr | Diastereo‐ and Enantioselective Reductive Mannich‐type Reaction of α,β‐Unsaturated Carboxylic Acids to Ketimines: A Direct Entry to Unprotected β
(2,3,3)‐Amino Acids |
title_full_unstemmed | Diastereo‐ and Enantioselective Reductive Mannich‐type Reaction of α,β‐Unsaturated Carboxylic Acids to Ketimines: A Direct Entry to Unprotected β
(2,3,3)‐Amino Acids |
title_short | Diastereo‐ and Enantioselective Reductive Mannich‐type Reaction of α,β‐Unsaturated Carboxylic Acids to Ketimines: A Direct Entry to Unprotected β
(2,3,3)‐Amino Acids |
title_sort | diastereo‐ and enantioselective reductive mannich‐type reaction of α,β‐unsaturated carboxylic acids to ketimines: a direct entry to unprotected β
(2,3,3)‐amino acids |
topic | Research Articles |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10107894/ https://www.ncbi.nlm.nih.gov/pubmed/36341524 http://dx.doi.org/10.1002/chem.202202575 |
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