Preparation of Chiral Enantioenriched Densely Substituted Cyclopropyl Azoles, Amines, and Ethers via Formal S(N)2′ Substitution of Bromocylopropanes

Enantiomerically enriched cyclopropyl ethers, amines, and cyclopropylazole derivatives possessing three stereogenic carbon atoms in a small cycle are obtained via the diastereoselective, formal nucleophilic substitution of chiral, non-racemic bromocyclopropanes. The key feature of this methodology i...

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Autores principales: Straub, Hillary, Ryabchuk, Pavel, Rubina, Marina, Rubin, Michael
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9609026/
https://www.ncbi.nlm.nih.gov/pubmed/36296663
http://dx.doi.org/10.3390/molecules27207069
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author Straub, Hillary
Ryabchuk, Pavel
Rubina, Marina
Rubin, Michael
author_facet Straub, Hillary
Ryabchuk, Pavel
Rubina, Marina
Rubin, Michael
author_sort Straub, Hillary
collection PubMed
description Enantiomerically enriched cyclopropyl ethers, amines, and cyclopropylazole derivatives possessing three stereogenic carbon atoms in a small cycle are obtained via the diastereoselective, formal nucleophilic substitution of chiral, non-racemic bromocyclopropanes. The key feature of this methodology is the utilization of the chiral center of the cyclopropene intermediate, which governs the configuration of the two adjacent stereocenters that are successively installed via 1,4-addition/epimerization sequence.
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spelling pubmed-96090262022-10-28 Preparation of Chiral Enantioenriched Densely Substituted Cyclopropyl Azoles, Amines, and Ethers via Formal S(N)2′ Substitution of Bromocylopropanes Straub, Hillary Ryabchuk, Pavel Rubina, Marina Rubin, Michael Molecules Article Enantiomerically enriched cyclopropyl ethers, amines, and cyclopropylazole derivatives possessing three stereogenic carbon atoms in a small cycle are obtained via the diastereoselective, formal nucleophilic substitution of chiral, non-racemic bromocyclopropanes. The key feature of this methodology is the utilization of the chiral center of the cyclopropene intermediate, which governs the configuration of the two adjacent stereocenters that are successively installed via 1,4-addition/epimerization sequence. MDPI 2022-10-20 /pmc/articles/PMC9609026/ /pubmed/36296663 http://dx.doi.org/10.3390/molecules27207069 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
Straub, Hillary
Ryabchuk, Pavel
Rubina, Marina
Rubin, Michael
Preparation of Chiral Enantioenriched Densely Substituted Cyclopropyl Azoles, Amines, and Ethers via Formal S(N)2′ Substitution of Bromocylopropanes
title Preparation of Chiral Enantioenriched Densely Substituted Cyclopropyl Azoles, Amines, and Ethers via Formal S(N)2′ Substitution of Bromocylopropanes
title_full Preparation of Chiral Enantioenriched Densely Substituted Cyclopropyl Azoles, Amines, and Ethers via Formal S(N)2′ Substitution of Bromocylopropanes
title_fullStr Preparation of Chiral Enantioenriched Densely Substituted Cyclopropyl Azoles, Amines, and Ethers via Formal S(N)2′ Substitution of Bromocylopropanes
title_full_unstemmed Preparation of Chiral Enantioenriched Densely Substituted Cyclopropyl Azoles, Amines, and Ethers via Formal S(N)2′ Substitution of Bromocylopropanes
title_short Preparation of Chiral Enantioenriched Densely Substituted Cyclopropyl Azoles, Amines, and Ethers via Formal S(N)2′ Substitution of Bromocylopropanes
title_sort preparation of chiral enantioenriched densely substituted cyclopropyl azoles, amines, and ethers via formal s(n)2′ substitution of bromocylopropanes
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9609026/
https://www.ncbi.nlm.nih.gov/pubmed/36296663
http://dx.doi.org/10.3390/molecules27207069
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