Borylated Cyclopropanes as Spring-Loaded Entities: Access to Vicinal Tertiary and Quaternary Carbon Stereocenters in Acyclic Systems

[Image: see text] Herein, we present the formation of acyclic frameworks bearing two consecutive stereocenters of either tertiary or quaternary nature starting from easily accessible cyclopropenes. This holistic approach involves a regio- and diastereoselective hydro- or carboborylation of substitut...

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Autores principales: Augustin, André U., Di Silvio, Sergio, Marek, Ilan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9479080/
https://www.ncbi.nlm.nih.gov/pubmed/36041738
http://dx.doi.org/10.1021/jacs.2c07394
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author Augustin, André U.
Di Silvio, Sergio
Marek, Ilan
author_facet Augustin, André U.
Di Silvio, Sergio
Marek, Ilan
author_sort Augustin, André U.
collection PubMed
description [Image: see text] Herein, we present the formation of acyclic frameworks bearing two consecutive stereocenters of either tertiary or quaternary nature starting from easily accessible cyclopropenes. This holistic approach involves a regio- and diastereoselective hydro- or carboborylation of substituted cyclopropenyl esters. Formation of boronate complexes of the latter via the addition of nucleophiles and subsequent stereospecific 1,2-migration with carbon–carbon bond cleavage delivered the title compounds.
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spelling pubmed-94790802022-09-17 Borylated Cyclopropanes as Spring-Loaded Entities: Access to Vicinal Tertiary and Quaternary Carbon Stereocenters in Acyclic Systems Augustin, André U. Di Silvio, Sergio Marek, Ilan J Am Chem Soc [Image: see text] Herein, we present the formation of acyclic frameworks bearing two consecutive stereocenters of either tertiary or quaternary nature starting from easily accessible cyclopropenes. This holistic approach involves a regio- and diastereoselective hydro- or carboborylation of substituted cyclopropenyl esters. Formation of boronate complexes of the latter via the addition of nucleophiles and subsequent stereospecific 1,2-migration with carbon–carbon bond cleavage delivered the title compounds. American Chemical Society 2022-08-30 2022-09-14 /pmc/articles/PMC9479080/ /pubmed/36041738 http://dx.doi.org/10.1021/jacs.2c07394 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Augustin, André U.
Di Silvio, Sergio
Marek, Ilan
Borylated Cyclopropanes as Spring-Loaded Entities: Access to Vicinal Tertiary and Quaternary Carbon Stereocenters in Acyclic Systems
title Borylated Cyclopropanes as Spring-Loaded Entities: Access to Vicinal Tertiary and Quaternary Carbon Stereocenters in Acyclic Systems
title_full Borylated Cyclopropanes as Spring-Loaded Entities: Access to Vicinal Tertiary and Quaternary Carbon Stereocenters in Acyclic Systems
title_fullStr Borylated Cyclopropanes as Spring-Loaded Entities: Access to Vicinal Tertiary and Quaternary Carbon Stereocenters in Acyclic Systems
title_full_unstemmed Borylated Cyclopropanes as Spring-Loaded Entities: Access to Vicinal Tertiary and Quaternary Carbon Stereocenters in Acyclic Systems
title_short Borylated Cyclopropanes as Spring-Loaded Entities: Access to Vicinal Tertiary and Quaternary Carbon Stereocenters in Acyclic Systems
title_sort borylated cyclopropanes as spring-loaded entities: access to vicinal tertiary and quaternary carbon stereocenters in acyclic systems
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9479080/
https://www.ncbi.nlm.nih.gov/pubmed/36041738
http://dx.doi.org/10.1021/jacs.2c07394
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