Synthesis and Functionalization of Tertiary Propargylic Boronic Esters by Alkynyllithium-Mediated 1,2-Metalate Rearrangement of Borylated Cyclopropanes

[Image: see text] Implementing the use of alkynyllithium reagents in a stereospecific 1,2-metalate rearrangement-mediated ring opening of polysubstituted cyclopropyl boronic esters provides a variety of tertiary pinacol boranes bearing adjacent tertiary or quaternary carbon stereocenters with high l...

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Autores principales: Pavlíčková, Tereza, Stöckl, Yannick, Marek, Ilan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9791689/
https://www.ncbi.nlm.nih.gov/pubmed/36446049
http://dx.doi.org/10.1021/acs.orglett.2c03756
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author Pavlíčková, Tereza
Stöckl, Yannick
Marek, Ilan
author_facet Pavlíčková, Tereza
Stöckl, Yannick
Marek, Ilan
author_sort Pavlíčková, Tereza
collection PubMed
description [Image: see text] Implementing the use of alkynyllithium reagents in a stereospecific 1,2-metalate rearrangement-mediated ring opening of polysubstituted cyclopropyl boronic esters provides a variety of tertiary pinacol boranes bearing adjacent tertiary or quaternary carbon stereocenters with high levels of diastereomeric purity. The potential of this strategy was demonstrated through a selection of α- and γ-functionalization of the propargyl boronic esters.
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spelling pubmed-97916892022-12-27 Synthesis and Functionalization of Tertiary Propargylic Boronic Esters by Alkynyllithium-Mediated 1,2-Metalate Rearrangement of Borylated Cyclopropanes Pavlíčková, Tereza Stöckl, Yannick Marek, Ilan Org Lett [Image: see text] Implementing the use of alkynyllithium reagents in a stereospecific 1,2-metalate rearrangement-mediated ring opening of polysubstituted cyclopropyl boronic esters provides a variety of tertiary pinacol boranes bearing adjacent tertiary or quaternary carbon stereocenters with high levels of diastereomeric purity. The potential of this strategy was demonstrated through a selection of α- and γ-functionalization of the propargyl boronic esters. American Chemical Society 2022-11-29 2022-12-09 /pmc/articles/PMC9791689/ /pubmed/36446049 http://dx.doi.org/10.1021/acs.orglett.2c03756 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 Pavlíčková, Tereza
Stöckl, Yannick
Marek, Ilan
Synthesis and Functionalization of Tertiary Propargylic Boronic Esters by Alkynyllithium-Mediated 1,2-Metalate Rearrangement of Borylated Cyclopropanes
title Synthesis and Functionalization of Tertiary Propargylic Boronic Esters by Alkynyllithium-Mediated 1,2-Metalate Rearrangement of Borylated Cyclopropanes
title_full Synthesis and Functionalization of Tertiary Propargylic Boronic Esters by Alkynyllithium-Mediated 1,2-Metalate Rearrangement of Borylated Cyclopropanes
title_fullStr Synthesis and Functionalization of Tertiary Propargylic Boronic Esters by Alkynyllithium-Mediated 1,2-Metalate Rearrangement of Borylated Cyclopropanes
title_full_unstemmed Synthesis and Functionalization of Tertiary Propargylic Boronic Esters by Alkynyllithium-Mediated 1,2-Metalate Rearrangement of Borylated Cyclopropanes
title_short Synthesis and Functionalization of Tertiary Propargylic Boronic Esters by Alkynyllithium-Mediated 1,2-Metalate Rearrangement of Borylated Cyclopropanes
title_sort synthesis and functionalization of tertiary propargylic boronic esters by alkynyllithium-mediated 1,2-metalate rearrangement of borylated cyclopropanes
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9791689/
https://www.ncbi.nlm.nih.gov/pubmed/36446049
http://dx.doi.org/10.1021/acs.orglett.2c03756
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