Directed Diastereoselective Cyclopropanation and Epoxidation of Alkenyl Cyclopropyl Carbinol Derivatives

[Image: see text] We report the directed diastereoselective Simmons–Smith cyclopropanation and vanadium-catalyzed epoxidation reactions of alkenyl cyclopropyl carbinol derivatives. The reaction furnished densely substituted stereodefined bicyclopropanes and cyclopropyl oxiranes as a single diastereo...

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Autores principales: Cohen, Anthony, Siddaraju, Yogesh, Marek, Ilan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9743385/
https://www.ncbi.nlm.nih.gov/pubmed/36354275
http://dx.doi.org/10.1021/acs.orglett.2c03305
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author Cohen, Anthony
Siddaraju, Yogesh
Marek, Ilan
author_facet Cohen, Anthony
Siddaraju, Yogesh
Marek, Ilan
author_sort Cohen, Anthony
collection PubMed
description [Image: see text] We report the directed diastereoselective Simmons–Smith cyclopropanation and vanadium-catalyzed epoxidation reactions of alkenyl cyclopropyl carbinol derivatives. The reaction furnished densely substituted stereodefined bicyclopropanes and cyclopropyl oxiranes as a single diastereomer in each case. The remarkable selectivity is obtained thanks to the rigidity of the cyclopropyl core, allowing diastereoselective reactions on the alkenyl moiety. This emphasizes the uniqueness of the cyclopropyl ring as a central platform in stereoselective synthesis.
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spelling pubmed-97433852022-12-13 Directed Diastereoselective Cyclopropanation and Epoxidation of Alkenyl Cyclopropyl Carbinol Derivatives Cohen, Anthony Siddaraju, Yogesh Marek, Ilan Org Lett [Image: see text] We report the directed diastereoselective Simmons–Smith cyclopropanation and vanadium-catalyzed epoxidation reactions of alkenyl cyclopropyl carbinol derivatives. The reaction furnished densely substituted stereodefined bicyclopropanes and cyclopropyl oxiranes as a single diastereomer in each case. The remarkable selectivity is obtained thanks to the rigidity of the cyclopropyl core, allowing diastereoselective reactions on the alkenyl moiety. This emphasizes the uniqueness of the cyclopropyl ring as a central platform in stereoselective synthesis. American Chemical Society 2022-11-10 2022-11-18 /pmc/articles/PMC9743385/ /pubmed/36354275 http://dx.doi.org/10.1021/acs.orglett.2c03305 Text en © 2022 American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Cohen, Anthony
Siddaraju, Yogesh
Marek, Ilan
Directed Diastereoselective Cyclopropanation and Epoxidation of Alkenyl Cyclopropyl Carbinol Derivatives
title Directed Diastereoselective Cyclopropanation and Epoxidation of Alkenyl Cyclopropyl Carbinol Derivatives
title_full Directed Diastereoselective Cyclopropanation and Epoxidation of Alkenyl Cyclopropyl Carbinol Derivatives
title_fullStr Directed Diastereoselective Cyclopropanation and Epoxidation of Alkenyl Cyclopropyl Carbinol Derivatives
title_full_unstemmed Directed Diastereoselective Cyclopropanation and Epoxidation of Alkenyl Cyclopropyl Carbinol Derivatives
title_short Directed Diastereoselective Cyclopropanation and Epoxidation of Alkenyl Cyclopropyl Carbinol Derivatives
title_sort directed diastereoselective cyclopropanation and epoxidation of alkenyl cyclopropyl carbinol derivatives
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9743385/
https://www.ncbi.nlm.nih.gov/pubmed/36354275
http://dx.doi.org/10.1021/acs.orglett.2c03305
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AT marekilan directeddiastereoselectivecyclopropanationandepoxidationofalkenylcyclopropylcarbinolderivatives

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