Stereoselective Construction of Tertiary Homoallyl Alcohols and Ethers by Nucleophilic Substitution at Quaternary Carbon Stereocenters

An efficient method for the stereoselective construction of tertiary C−O bonds via a stereoinvertive nucleophilic substitution at the quaternary carbon stereocenter of cyclopropyl carbinol derivatives using water, alcohols and phenols as nucleophiles has been developed. This substitution reaction pr...

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Autores principales: Chen, Xu, Patel, Kaushalendra, Marek, Ilan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
Materias:
Research Articles
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10107121/
https://www.ncbi.nlm.nih.gov/pubmed/36413111
http://dx.doi.org/10.1002/anie.202212425
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author Chen, Xu
Patel, Kaushalendra
Marek, Ilan
author_facet Chen, Xu
Patel, Kaushalendra
Marek, Ilan
author_sort Chen, Xu
collection PubMed
description An efficient method for the stereoselective construction of tertiary C−O bonds via a stereoinvertive nucleophilic substitution at the quaternary carbon stereocenter of cyclopropyl carbinol derivatives using water, alcohols and phenols as nucleophiles has been developed. This substitution reaction proceeds under mild conditions and tolerates several functional groups, providing a new access to the stereoselective formation of highly congested tertiary homoallyl alcohols and ethers.
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spelling pubmed-101071212023-04-18 Stereoselective Construction of Tertiary Homoallyl Alcohols and Ethers by Nucleophilic Substitution at Quaternary Carbon Stereocenters Chen, Xu Patel, Kaushalendra Marek, Ilan Angew Chem Int Ed Engl Research Articles An efficient method for the stereoselective construction of tertiary C−O bonds via a stereoinvertive nucleophilic substitution at the quaternary carbon stereocenter of cyclopropyl carbinol derivatives using water, alcohols and phenols as nucleophiles has been developed. This substitution reaction proceeds under mild conditions and tolerates several functional groups, providing a new access to the stereoselective formation of highly congested tertiary homoallyl alcohols and ethers. John Wiley and Sons Inc. 2022-12-13 2023-01-16 /pmc/articles/PMC10107121/ /pubmed/36413111 http://dx.doi.org/10.1002/anie.202212425 Text en © 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH https://creativecommons.org/licenses/by-nc-nd/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ (https://creativecommons.org/licenses/by-nc-nd/4.0/) License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Research Articles
Chen, Xu
Patel, Kaushalendra
Marek, Ilan
Stereoselective Construction of Tertiary Homoallyl Alcohols and Ethers by Nucleophilic Substitution at Quaternary Carbon Stereocenters
title Stereoselective Construction of Tertiary Homoallyl Alcohols and Ethers by Nucleophilic Substitution at Quaternary Carbon Stereocenters
title_full Stereoselective Construction of Tertiary Homoallyl Alcohols and Ethers by Nucleophilic Substitution at Quaternary Carbon Stereocenters
title_fullStr Stereoselective Construction of Tertiary Homoallyl Alcohols and Ethers by Nucleophilic Substitution at Quaternary Carbon Stereocenters
title_full_unstemmed Stereoselective Construction of Tertiary Homoallyl Alcohols and Ethers by Nucleophilic Substitution at Quaternary Carbon Stereocenters
title_short Stereoselective Construction of Tertiary Homoallyl Alcohols and Ethers by Nucleophilic Substitution at Quaternary Carbon Stereocenters
title_sort stereoselective construction of tertiary homoallyl alcohols and ethers by nucleophilic substitution at quaternary carbon stereocenters
topic Research Articles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10107121/
https://www.ncbi.nlm.nih.gov/pubmed/36413111
http://dx.doi.org/10.1002/anie.202212425
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AT patelkaushalendra stereoselectiveconstructionoftertiaryhomoallylalcoholsandethersbynucleophilicsubstitutionatquaternarycarbonstereocenters
AT marekilan stereoselectiveconstructionoftertiaryhomoallylalcoholsandethersbynucleophilicsubstitutionatquaternarycarbonstereocenters

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