Facile Formation of β-Hydroxyboronate Esters by a Cu-Catalyzed Diboration/Matteson Homologation Sequence

[Image: see text] The copper-catalyzed diboration of aldehydes was used in conjunction with the Matteson homologation, providing the efficient synthesis of β-hydroxyboronate esters. The oxygen-bound boronate ester was found to play a key role in mediating the homologation reaction, which was compare...

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Autores principales: Moore, Cameron M., Medina, Casey R., Cannamela, Peter C., McIntosh, Melissa L., Ferber, Carl J., Roering, Andrew J., Clark, Timothy B.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4260635/
https://www.ncbi.nlm.nih.gov/pubmed/25412356
http://dx.doi.org/10.1021/ol502767m
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author Moore, Cameron M.
Medina, Casey R.
Cannamela, Peter C.
McIntosh, Melissa L.
Ferber, Carl J.
Roering, Andrew J.
Clark, Timothy B.
author_facet Moore, Cameron M.
Medina, Casey R.
Cannamela, Peter C.
McIntosh, Melissa L.
Ferber, Carl J.
Roering, Andrew J.
Clark, Timothy B.
author_sort Moore, Cameron M.
collection PubMed
description [Image: see text] The copper-catalyzed diboration of aldehydes was used in conjunction with the Matteson homologation, providing the efficient synthesis of β-hydroxyboronate esters. The oxygen-bound boronate ester was found to play a key role in mediating the homologation reaction, which was compared to the α-hydroxyboronate ester (isolated hydrolysis product). The synthetic utility of the diboration/homologation sequence was demonstrated through the oxidation of one product to provide a 1,2-diol.
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spelling pubmed-42606352015-11-20 Facile Formation of β-Hydroxyboronate Esters by a Cu-Catalyzed Diboration/Matteson Homologation Sequence Moore, Cameron M. Medina, Casey R. Cannamela, Peter C. McIntosh, Melissa L. Ferber, Carl J. Roering, Andrew J. Clark, Timothy B. Org Lett [Image: see text] The copper-catalyzed diboration of aldehydes was used in conjunction with the Matteson homologation, providing the efficient synthesis of β-hydroxyboronate esters. The oxygen-bound boronate ester was found to play a key role in mediating the homologation reaction, which was compared to the α-hydroxyboronate ester (isolated hydrolysis product). The synthetic utility of the diboration/homologation sequence was demonstrated through the oxidation of one product to provide a 1,2-diol. American Chemical Society 2014-11-20 2014-12-05 /pmc/articles/PMC4260635/ /pubmed/25412356 http://dx.doi.org/10.1021/ol502767m Text en Copyright © 2014 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Moore, Cameron M.
Medina, Casey R.
Cannamela, Peter C.
McIntosh, Melissa L.
Ferber, Carl J.
Roering, Andrew J.
Clark, Timothy B.
Facile Formation of β-Hydroxyboronate Esters by a Cu-Catalyzed Diboration/Matteson Homologation Sequence
title Facile Formation of β-Hydroxyboronate Esters by a Cu-Catalyzed Diboration/Matteson Homologation Sequence
title_full Facile Formation of β-Hydroxyboronate Esters by a Cu-Catalyzed Diboration/Matteson Homologation Sequence
title_fullStr Facile Formation of β-Hydroxyboronate Esters by a Cu-Catalyzed Diboration/Matteson Homologation Sequence
title_full_unstemmed Facile Formation of β-Hydroxyboronate Esters by a Cu-Catalyzed Diboration/Matteson Homologation Sequence
title_short Facile Formation of β-Hydroxyboronate Esters by a Cu-Catalyzed Diboration/Matteson Homologation Sequence
title_sort facile formation of β-hydroxyboronate esters by a cu-catalyzed diboration/matteson homologation sequence
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4260635/
https://www.ncbi.nlm.nih.gov/pubmed/25412356
http://dx.doi.org/10.1021/ol502767m
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