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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...

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Detalles Bibliográficos
Autores principales: Homma, Chihiro, Takeshima, Aika, Kano, Taichi, Maruoka, Keiji
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2020
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.
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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
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