Stereo- and Regiocontrolled Methylboration of Terminal Alkynes

[Image: see text] A scalable and operationally simple synthesis of trisubstituted alkenyl boronic esters has been achieved using a Zr-catalyzed carboalumination of terminal alkynes followed by in situ transmetalation with i-PrOBpin. The products are formed in good yields and with excellent regiosele...

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Autores principales: Zhurakovskyi, Oleksandr, Dias, Rafael M. P., Noble, Adam, Aggarwal, Varinder K.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2018
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6007961/
https://www.ncbi.nlm.nih.gov/pubmed/29741904
http://dx.doi.org/10.1021/acs.orglett.8b01252
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author Zhurakovskyi, Oleksandr
Dias, Rafael M. P.
Noble, Adam
Aggarwal, Varinder K.
author_facet Zhurakovskyi, Oleksandr
Dias, Rafael M. P.
Noble, Adam
Aggarwal, Varinder K.
author_sort Zhurakovskyi, Oleksandr
collection PubMed
description [Image: see text] A scalable and operationally simple synthesis of trisubstituted alkenyl boronic esters has been achieved using a Zr-catalyzed carboalumination of terminal alkynes followed by in situ transmetalation with i-PrOBpin. The products are formed in good yields and with excellent regioselectivity and perfect stereoselectivity. The new procedure provides a significant improvement over the previously reported syntheses.
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spelling pubmed-60079612018-06-20 Stereo- and Regiocontrolled Methylboration of Terminal Alkynes Zhurakovskyi, Oleksandr Dias, Rafael M. P. Noble, Adam Aggarwal, Varinder K. Org Lett [Image: see text] A scalable and operationally simple synthesis of trisubstituted alkenyl boronic esters has been achieved using a Zr-catalyzed carboalumination of terminal alkynes followed by in situ transmetalation with i-PrOBpin. The products are formed in good yields and with excellent regioselectivity and perfect stereoselectivity. The new procedure provides a significant improvement over the previously reported syntheses. American Chemical Society 2018-05-09 2018-05-18 /pmc/articles/PMC6007961/ /pubmed/29741904 http://dx.doi.org/10.1021/acs.orglett.8b01252 Text en Copyright © 2018 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
spellingShingle Zhurakovskyi, Oleksandr
Dias, Rafael M. P.
Noble, Adam
Aggarwal, Varinder K.
Stereo- and Regiocontrolled Methylboration of Terminal Alkynes
title Stereo- and Regiocontrolled Methylboration of Terminal Alkynes
title_full Stereo- and Regiocontrolled Methylboration of Terminal Alkynes
title_fullStr Stereo- and Regiocontrolled Methylboration of Terminal Alkynes
title_full_unstemmed Stereo- and Regiocontrolled Methylboration of Terminal Alkynes
title_short Stereo- and Regiocontrolled Methylboration of Terminal Alkynes
title_sort stereo- and regiocontrolled methylboration of terminal alkynes
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6007961/
https://www.ncbi.nlm.nih.gov/pubmed/29741904
http://dx.doi.org/10.1021/acs.orglett.8b01252
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