Resolution of a Configurationally Stable Hetero[4]helicene

We have developed an efficient chemical resolution of racemic hydroxy substituted dithia-aza[4]helicenes (DTA[4]H) 1(OH) using enantiopure acids as resolving agents. The better diastereomeric separation was achieved on esters prepared with (1S)-(−)-camphanic acid. Subsequent simple manipulations pro...

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Detalles Bibliográficos
Autores principales: Lupi, Michela, Onori, Martina, Menichetti, Stefano, Abbate, Sergio, Longhi, Giovanna, Viglianisi, Caterina
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8874595/
https://www.ncbi.nlm.nih.gov/pubmed/35208947
http://dx.doi.org/10.3390/molecules27041160
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author Lupi, Michela
Onori, Martina
Menichetti, Stefano
Abbate, Sergio
Longhi, Giovanna
Viglianisi, Caterina
author_facet Lupi, Michela
Onori, Martina
Menichetti, Stefano
Abbate, Sergio
Longhi, Giovanna
Viglianisi, Caterina
author_sort Lupi, Michela
collection PubMed
description We have developed an efficient chemical resolution of racemic hydroxy substituted dithia-aza[4]helicenes (DTA[4]H) 1(OH) using enantiopure acids as resolving agents. The better diastereomeric separation was achieved on esters prepared with (1S)-(−)-camphanic acid. Subsequent simple manipulations produced highly optically pure (≥ 99% enantiomeric excess) (P) and (M)-1(OH) in good yields. The role of the position where the chiral auxiliary is inserted (cape- vs. bay-zone) and the structure of the enantiopure acid used on successful resolution are discussed.
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spelling pubmed-88745952022-02-26 Resolution of a Configurationally Stable Hetero[4]helicene Lupi, Michela Onori, Martina Menichetti, Stefano Abbate, Sergio Longhi, Giovanna Viglianisi, Caterina Molecules Article We have developed an efficient chemical resolution of racemic hydroxy substituted dithia-aza[4]helicenes (DTA[4]H) 1(OH) using enantiopure acids as resolving agents. The better diastereomeric separation was achieved on esters prepared with (1S)-(−)-camphanic acid. Subsequent simple manipulations produced highly optically pure (≥ 99% enantiomeric excess) (P) and (M)-1(OH) in good yields. The role of the position where the chiral auxiliary is inserted (cape- vs. bay-zone) and the structure of the enantiopure acid used on successful resolution are discussed. MDPI 2022-02-09 /pmc/articles/PMC8874595/ /pubmed/35208947 http://dx.doi.org/10.3390/molecules27041160 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Lupi, Michela
Onori, Martina
Menichetti, Stefano
Abbate, Sergio
Longhi, Giovanna
Viglianisi, Caterina
Resolution of a Configurationally Stable Hetero[4]helicene
title Resolution of a Configurationally Stable Hetero[4]helicene
title_full Resolution of a Configurationally Stable Hetero[4]helicene
title_fullStr Resolution of a Configurationally Stable Hetero[4]helicene
title_full_unstemmed Resolution of a Configurationally Stable Hetero[4]helicene
title_short Resolution of a Configurationally Stable Hetero[4]helicene
title_sort resolution of a configurationally stable hetero[4]helicene
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8874595/
https://www.ncbi.nlm.nih.gov/pubmed/35208947
http://dx.doi.org/10.3390/molecules27041160
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AT menichettistefano resolutionofaconfigurationallystablehetero4helicene
AT abbatesergio resolutionofaconfigurationallystablehetero4helicene
AT longhigiovanna resolutionofaconfigurationallystablehetero4helicene
AT viglianisicaterina resolutionofaconfigurationallystablehetero4helicene

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