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Construction of chiral α-tert-amine scaffolds via amine-catalyzed asymmetric Mannich reactions of alkyl-substituted ketimines
Stereoselective Mannich reactions of aldehydes with ketimines provide chiral β-amino aldehydes that bear an α-tert-amine moiety. However, the structural variation of the ketimines is limited due to the formation of inseparable E/Z isomers, low reactivity, and other synthetic difficulties. In this st...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8179053/ https://www.ncbi.nlm.nih.gov/pubmed/34163907 http://dx.doi.org/10.1039/d0sc05269h |
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author | Homma, Chihiro Takeshima, Aika Kano, Taichi Maruoka, Keiji |
author_facet | Homma, Chihiro Takeshima, Aika Kano, Taichi Maruoka, Keiji |
author_sort | Homma, Chihiro |
collection | PubMed |
description | Stereoselective Mannich reactions of aldehydes with ketimines provide chiral β-amino aldehydes that bear an α-tert-amine moiety. However, the structural variation of the ketimines is limited due to the formation of inseparable E/Z isomers, low reactivity, and other synthetic difficulties. In this study, a highly diastereodivergent synthesis of hitherto difficult-to-access β-amino aldehydes that bear a chiral α-tert-amine moiety was achieved using the amine-catalyzed Mannich reactions of aldehydes with less-activated Z-ketimines that bear both alkyl and alkynyl groups. |
format | Online Article Text |
id | pubmed-8179053 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-81790532021-06-22 Construction of chiral α-tert-amine scaffolds via amine-catalyzed asymmetric Mannich reactions of alkyl-substituted ketimines Homma, Chihiro Takeshima, Aika Kano, Taichi Maruoka, Keiji Chem Sci Chemistry Stereoselective Mannich reactions of aldehydes with ketimines provide chiral β-amino aldehydes that bear an α-tert-amine moiety. However, the structural variation of the ketimines is limited due to the formation of inseparable E/Z isomers, low reactivity, and other synthetic difficulties. In this study, a highly diastereodivergent synthesis of hitherto difficult-to-access β-amino aldehydes that bear a chiral α-tert-amine moiety was achieved using the amine-catalyzed Mannich reactions of aldehydes with less-activated Z-ketimines that bear both alkyl and alkynyl groups. The Royal Society of Chemistry 2020-11-27 /pmc/articles/PMC8179053/ /pubmed/34163907 http://dx.doi.org/10.1039/d0sc05269h Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/ |
spellingShingle | Chemistry Homma, Chihiro Takeshima, Aika Kano, Taichi Maruoka, Keiji Construction of chiral α-tert-amine scaffolds via amine-catalyzed asymmetric Mannich reactions of alkyl-substituted ketimines |
title | Construction of chiral α-tert-amine scaffolds via amine-catalyzed asymmetric Mannich reactions of alkyl-substituted ketimines |
title_full | Construction of chiral α-tert-amine scaffolds via amine-catalyzed asymmetric Mannich reactions of alkyl-substituted ketimines |
title_fullStr | Construction of chiral α-tert-amine scaffolds via amine-catalyzed asymmetric Mannich reactions of alkyl-substituted ketimines |
title_full_unstemmed | Construction of chiral α-tert-amine scaffolds via amine-catalyzed asymmetric Mannich reactions of alkyl-substituted ketimines |
title_short | Construction of chiral α-tert-amine scaffolds via amine-catalyzed asymmetric Mannich reactions of alkyl-substituted ketimines |
title_sort | construction of chiral α-tert-amine scaffolds via amine-catalyzed asymmetric mannich reactions of alkyl-substituted ketimines |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8179053/ https://www.ncbi.nlm.nih.gov/pubmed/34163907 http://dx.doi.org/10.1039/d0sc05269h |
work_keys_str_mv | AT hommachihiro constructionofchiralatertaminescaffoldsviaaminecatalyzedasymmetricmannichreactionsofalkylsubstitutedketimines AT takeshimaaika constructionofchiralatertaminescaffoldsviaaminecatalyzedasymmetricmannichreactionsofalkylsubstitutedketimines AT kanotaichi constructionofchiralatertaminescaffoldsviaaminecatalyzedasymmetricmannichreactionsofalkylsubstitutedketimines AT maruokakeiji constructionofchiralatertaminescaffoldsviaaminecatalyzedasymmetricmannichreactionsofalkylsubstitutedketimines |