Chiral Cu(II)-catalyzed enantioselective β-borylation of α,β-unsaturated nitriles in water

The promising performance of copper(II) complexes was demonstrated for asymmetric boron conjugate addition to α,β-unsaturated nitriles in water. The catalyst system, which consisted of Cu(OAc)(2) and a chiral 2,2′-bipyridine ligand, enabled β-borylation and chiral induction in water. Subsequent prot...

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Autores principales: Zhu, Lei, Kitanosono, Taku, Xu, Pengyu, Kobayashi, Shū
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2015
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4661013/
https://www.ncbi.nlm.nih.gov/pubmed/26664621
http://dx.doi.org/10.3762/bjoc.11.217
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author Zhu, Lei
Kitanosono, Taku
Xu, Pengyu
Kobayashi, Shū
author_facet Zhu, Lei
Kitanosono, Taku
Xu, Pengyu
Kobayashi, Shū
author_sort Zhu, Lei
collection PubMed
description The promising performance of copper(II) complexes was demonstrated for asymmetric boron conjugate addition to α,β-unsaturated nitriles in water. The catalyst system, which consisted of Cu(OAc)(2) and a chiral 2,2′-bipyridine ligand, enabled β-borylation and chiral induction in water. Subsequent protonation, which was accelerated in aqueous medium, led to high activity of this asymmetric catalysis. Both solid and liquid substrates were suitable despite being insoluble in water.
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spelling pubmed-46610132015-12-09 Chiral Cu(II)-catalyzed enantioselective β-borylation of α,β-unsaturated nitriles in water Zhu, Lei Kitanosono, Taku Xu, Pengyu Kobayashi, Shū Beilstein J Org Chem Full Research Paper The promising performance of copper(II) complexes was demonstrated for asymmetric boron conjugate addition to α,β-unsaturated nitriles in water. The catalyst system, which consisted of Cu(OAc)(2) and a chiral 2,2′-bipyridine ligand, enabled β-borylation and chiral induction in water. Subsequent protonation, which was accelerated in aqueous medium, led to high activity of this asymmetric catalysis. Both solid and liquid substrates were suitable despite being insoluble in water. Beilstein-Institut 2015-10-27 /pmc/articles/PMC4661013/ /pubmed/26664621 http://dx.doi.org/10.3762/bjoc.11.217 Text en Copyright © 2015, Zhu et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Zhu, Lei
Kitanosono, Taku
Xu, Pengyu
Kobayashi, Shū
Chiral Cu(II)-catalyzed enantioselective β-borylation of α,β-unsaturated nitriles in water
title Chiral Cu(II)-catalyzed enantioselective β-borylation of α,β-unsaturated nitriles in water
title_full Chiral Cu(II)-catalyzed enantioselective β-borylation of α,β-unsaturated nitriles in water
title_fullStr Chiral Cu(II)-catalyzed enantioselective β-borylation of α,β-unsaturated nitriles in water
title_full_unstemmed Chiral Cu(II)-catalyzed enantioselective β-borylation of α,β-unsaturated nitriles in water
title_short Chiral Cu(II)-catalyzed enantioselective β-borylation of α,β-unsaturated nitriles in water
title_sort chiral cu(ii)-catalyzed enantioselective β-borylation of α,β-unsaturated nitriles in water
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4661013/
https://www.ncbi.nlm.nih.gov/pubmed/26664621
http://dx.doi.org/10.3762/bjoc.11.217
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