Parallel kinetic resolution of aziridines via chiral phosphoric acid-catalyzed apparent hydrolytic ring-opening

We report a chiral phosphoric acid catalyzed apparent hydrolytic ring-opening reaction of racemic aziridines in a regiodivergent parallel kinetic resolution manner. Harnessing the acyloxy-assisted strategy, the highly stereocontrolled nucleophilic ring-opening of aziridines with water is achieved. D...

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Autores principales: Liu, Juan, Du, Yi-Ying, He, Yu-Shi, Liang, Yan, Liu, Shang-Zhong, Li, Yi-Yi, Cao, Yi-Ming
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/PMC10631200/
https://www.ncbi.nlm.nih.gov/pubmed/37969581
http://dx.doi.org/10.1039/d3sc03899h
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author Liu, Juan
Du, Yi-Ying
He, Yu-Shi
Liang, Yan
Liu, Shang-Zhong
Li, Yi-Yi
Cao, Yi-Ming
author_facet Liu, Juan
Du, Yi-Ying
He, Yu-Shi
Liang, Yan
Liu, Shang-Zhong
Li, Yi-Yi
Cao, Yi-Ming
author_sort Liu, Juan
collection PubMed
description We report a chiral phosphoric acid catalyzed apparent hydrolytic ring-opening reaction of racemic aziridines in a regiodivergent parallel kinetic resolution manner. Harnessing the acyloxy-assisted strategy, the highly stereocontrolled nucleophilic ring-opening of aziridines with water is achieved. Different kinds of aziridines are applicable in the process, giving a variety of enantioenriched aromatic or aliphatic amino alcohols with up to 99% yields and up to >99.5 : 0.5 enantiomeric ratio. Preliminary mechanistic study as well as product elaborations were inducted as well.
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spelling pubmed-106312002023-11-15 Parallel kinetic resolution of aziridines via chiral phosphoric acid-catalyzed apparent hydrolytic ring-opening Liu, Juan Du, Yi-Ying He, Yu-Shi Liang, Yan Liu, Shang-Zhong Li, Yi-Yi Cao, Yi-Ming Chem Sci Chemistry We report a chiral phosphoric acid catalyzed apparent hydrolytic ring-opening reaction of racemic aziridines in a regiodivergent parallel kinetic resolution manner. Harnessing the acyloxy-assisted strategy, the highly stereocontrolled nucleophilic ring-opening of aziridines with water is achieved. Different kinds of aziridines are applicable in the process, giving a variety of enantioenriched aromatic or aliphatic amino alcohols with up to 99% yields and up to >99.5 : 0.5 enantiomeric ratio. Preliminary mechanistic study as well as product elaborations were inducted as well. The Royal Society of Chemistry 2023-10-12 /pmc/articles/PMC10631200/ /pubmed/37969581 http://dx.doi.org/10.1039/d3sc03899h Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Liu, Juan
Du, Yi-Ying
He, Yu-Shi
Liang, Yan
Liu, Shang-Zhong
Li, Yi-Yi
Cao, Yi-Ming
Parallel kinetic resolution of aziridines via chiral phosphoric acid-catalyzed apparent hydrolytic ring-opening
title Parallel kinetic resolution of aziridines via chiral phosphoric acid-catalyzed apparent hydrolytic ring-opening
title_full Parallel kinetic resolution of aziridines via chiral phosphoric acid-catalyzed apparent hydrolytic ring-opening
title_fullStr Parallel kinetic resolution of aziridines via chiral phosphoric acid-catalyzed apparent hydrolytic ring-opening
title_full_unstemmed Parallel kinetic resolution of aziridines via chiral phosphoric acid-catalyzed apparent hydrolytic ring-opening
title_short Parallel kinetic resolution of aziridines via chiral phosphoric acid-catalyzed apparent hydrolytic ring-opening
title_sort parallel kinetic resolution of aziridines via chiral phosphoric acid-catalyzed apparent hydrolytic ring-opening
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10631200/
https://www.ncbi.nlm.nih.gov/pubmed/37969581
http://dx.doi.org/10.1039/d3sc03899h
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