Chiral spirocyclic phosphoric acid-catalyzed enantioselective synthesis of heterotriarylmethanes bearing an amino acid moiety

We present herein an enantioselective protocol for the chiral phosphoric acid-catalyzed addition of 3-arylisoxazol-5-amines to highly reactive 3-methide-3H-pyrroles to provide a diverse range of heterotriarylmethanes bearing an amino acid moiety in good yields (up to 97%) and high enantioselectiviti...

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Detalles Bibliográficos
Autores principales: Jiaping, Jin, Woldegiorgis, Alemayehu Gashaw, Lin, Xufeng
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2023
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10285616/
https://www.ncbi.nlm.nih.gov/pubmed/37362600
http://dx.doi.org/10.1039/d3ra03480a
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author Jiaping, Jin
Woldegiorgis, Alemayehu Gashaw
Lin, Xufeng
author_facet Jiaping, Jin
Woldegiorgis, Alemayehu Gashaw
Lin, Xufeng
author_sort Jiaping, Jin
collection PubMed
description We present herein an enantioselective protocol for the chiral phosphoric acid-catalyzed addition of 3-arylisoxazol-5-amines to highly reactive 3-methide-3H-pyrroles to provide a diverse range of heterotriarylmethanes bearing an amino acid moiety in good yields (up to 97%) and high enantioselectivities (up to 93% ee) under mild conditions. The chiral spirocyclic phosphoric acid is crucial in converting the initial 1H-pyrrol-3-yl carbinols into reactive 3-methide-3H-pyrroles and obtaining the good enantiocontrol, thereby facilitating the desired enantioselective transformation.
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spelling pubmed-102856162023-06-23 Chiral spirocyclic phosphoric acid-catalyzed enantioselective synthesis of heterotriarylmethanes bearing an amino acid moiety Jiaping, Jin Woldegiorgis, Alemayehu Gashaw Lin, Xufeng RSC Adv Chemistry We present herein an enantioselective protocol for the chiral phosphoric acid-catalyzed addition of 3-arylisoxazol-5-amines to highly reactive 3-methide-3H-pyrroles to provide a diverse range of heterotriarylmethanes bearing an amino acid moiety in good yields (up to 97%) and high enantioselectivities (up to 93% ee) under mild conditions. The chiral spirocyclic phosphoric acid is crucial in converting the initial 1H-pyrrol-3-yl carbinols into reactive 3-methide-3H-pyrroles and obtaining the good enantiocontrol, thereby facilitating the desired enantioselective transformation. The Royal Society of Chemistry 2023-06-22 /pmc/articles/PMC10285616/ /pubmed/37362600 http://dx.doi.org/10.1039/d3ra03480a Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Jiaping, Jin
Woldegiorgis, Alemayehu Gashaw
Lin, Xufeng
Chiral spirocyclic phosphoric acid-catalyzed enantioselective synthesis of heterotriarylmethanes bearing an amino acid moiety
title Chiral spirocyclic phosphoric acid-catalyzed enantioselective synthesis of heterotriarylmethanes bearing an amino acid moiety
title_full Chiral spirocyclic phosphoric acid-catalyzed enantioselective synthesis of heterotriarylmethanes bearing an amino acid moiety
title_fullStr Chiral spirocyclic phosphoric acid-catalyzed enantioselective synthesis of heterotriarylmethanes bearing an amino acid moiety
title_full_unstemmed Chiral spirocyclic phosphoric acid-catalyzed enantioselective synthesis of heterotriarylmethanes bearing an amino acid moiety
title_short Chiral spirocyclic phosphoric acid-catalyzed enantioselective synthesis of heterotriarylmethanes bearing an amino acid moiety
title_sort chiral spirocyclic phosphoric acid-catalyzed enantioselective synthesis of heterotriarylmethanes bearing an amino acid moiety
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10285616/
https://www.ncbi.nlm.nih.gov/pubmed/37362600
http://dx.doi.org/10.1039/d3ra03480a
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AT woldegiorgisalemayehugashaw chiralspirocyclicphosphoricacidcatalyzedenantioselectivesynthesisofheterotriarylmethanesbearinganaminoacidmoiety
AT linxufeng chiralspirocyclicphosphoricacidcatalyzedenantioselectivesynthesisofheterotriarylmethanesbearinganaminoacidmoiety

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