A Catalytic Enantiotopic-Group-Selective Suzuki Reaction for the Construction of Chiral Organoboronates

[Image: see text] Catalytic enantiotopic-group-selective cross-couplings of achiral geminal bis(pinacolboronates) provide a route for the construction of nonracemic chiral organoboronates. In the presence of a chiral monodentate taddol-derived phosphoramidite ligand, these reactions occur with high...

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Autores principales: Sun, Chunrui, Potter, Bowman, Morken, James P.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4021567/
https://www.ncbi.nlm.nih.gov/pubmed/24564423
http://dx.doi.org/10.1021/ja500029w
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author Sun, Chunrui
Potter, Bowman
Morken, James P.
author_facet Sun, Chunrui
Potter, Bowman
Morken, James P.
author_sort Sun, Chunrui
collection PubMed
description [Image: see text] Catalytic enantiotopic-group-selective cross-couplings of achiral geminal bis(pinacolboronates) provide a route for the construction of nonracemic chiral organoboronates. In the presence of a chiral monodentate taddol-derived phosphoramidite ligand, these reactions occur with high levels of asymmetric induction. Mechanistic experiments with chiral (10)B-enriched geminal bis(boronates) suggest that the reaction occurs by a stereochemistry-determining transmetalation that occurs with inversion of configuration at carbon.
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spelling pubmed-40215672015-02-19 A Catalytic Enantiotopic-Group-Selective Suzuki Reaction for the Construction of Chiral Organoboronates Sun, Chunrui Potter, Bowman Morken, James P. J Am Chem Soc [Image: see text] Catalytic enantiotopic-group-selective cross-couplings of achiral geminal bis(pinacolboronates) provide a route for the construction of nonracemic chiral organoboronates. In the presence of a chiral monodentate taddol-derived phosphoramidite ligand, these reactions occur with high levels of asymmetric induction. Mechanistic experiments with chiral (10)B-enriched geminal bis(boronates) suggest that the reaction occurs by a stereochemistry-determining transmetalation that occurs with inversion of configuration at carbon. American Chemical Society 2014-02-19 2014-05-07 /pmc/articles/PMC4021567/ /pubmed/24564423 http://dx.doi.org/10.1021/ja500029w Text en Copyright © 2014 American Chemical Society
spellingShingle Sun, Chunrui
Potter, Bowman
Morken, James P.
A Catalytic Enantiotopic-Group-Selective Suzuki Reaction for the Construction of Chiral Organoboronates
title A Catalytic Enantiotopic-Group-Selective Suzuki Reaction for the Construction of Chiral Organoboronates
title_full A Catalytic Enantiotopic-Group-Selective Suzuki Reaction for the Construction of Chiral Organoboronates
title_fullStr A Catalytic Enantiotopic-Group-Selective Suzuki Reaction for the Construction of Chiral Organoboronates
title_full_unstemmed A Catalytic Enantiotopic-Group-Selective Suzuki Reaction for the Construction of Chiral Organoboronates
title_short A Catalytic Enantiotopic-Group-Selective Suzuki Reaction for the Construction of Chiral Organoboronates
title_sort catalytic enantiotopic-group-selective suzuki reaction for the construction of chiral organoboronates
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4021567/
https://www.ncbi.nlm.nih.gov/pubmed/24564423
http://dx.doi.org/10.1021/ja500029w
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