Copper-catalyzed enantioselective conjugate reduction of α,β-unsaturated esters with chiral phenol–carbene ligands

A chiral phenol–NHC ligand enabled the copper-catalyzed enantioselective conjugate reduction of α,β-unsaturated esters. The phenol moiety of the chiral NHC ligand played a critical role in producing the enantiomerically enriched products. The catalyst worked well for various (Z)-isomer substrates. O...

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Detalles Bibliográficos
Autores principales: Mimura, Shohei, Mizushima, Sho, Shimizu, Yohei, Sawamura, Masaya
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2020
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7136546/
https://www.ncbi.nlm.nih.gov/pubmed/32280383
http://dx.doi.org/10.3762/bjoc.16.50
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author Mimura, Shohei
Mizushima, Sho
Shimizu, Yohei
Sawamura, Masaya
author_facet Mimura, Shohei
Mizushima, Sho
Shimizu, Yohei
Sawamura, Masaya
author_sort Mimura, Shohei
collection PubMed
description A chiral phenol–NHC ligand enabled the copper-catalyzed enantioselective conjugate reduction of α,β-unsaturated esters. The phenol moiety of the chiral NHC ligand played a critical role in producing the enantiomerically enriched products. The catalyst worked well for various (Z)-isomer substrates. Opposite enantiomers were obtained from (Z)- and (E)-isomers, with a higher enantiomeric excess from the (Z)-isomer.
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spelling pubmed-71365462020-04-10 Copper-catalyzed enantioselective conjugate reduction of α,β-unsaturated esters with chiral phenol–carbene ligands Mimura, Shohei Mizushima, Sho Shimizu, Yohei Sawamura, Masaya Beilstein J Org Chem Full Research Paper A chiral phenol–NHC ligand enabled the copper-catalyzed enantioselective conjugate reduction of α,β-unsaturated esters. The phenol moiety of the chiral NHC ligand played a critical role in producing the enantiomerically enriched products. The catalyst worked well for various (Z)-isomer substrates. Opposite enantiomers were obtained from (Z)- and (E)-isomers, with a higher enantiomeric excess from the (Z)-isomer. Beilstein-Institut 2020-03-31 /pmc/articles/PMC7136546/ /pubmed/32280383 http://dx.doi.org/10.3762/bjoc.16.50 Text en Copyright © 2020, Mimura et al. https://creativecommons.org/licenses/by/4.0https://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/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited. 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
Mimura, Shohei
Mizushima, Sho
Shimizu, Yohei
Sawamura, Masaya
Copper-catalyzed enantioselective conjugate reduction of α,β-unsaturated esters with chiral phenol–carbene ligands
title Copper-catalyzed enantioselective conjugate reduction of α,β-unsaturated esters with chiral phenol–carbene ligands
title_full Copper-catalyzed enantioselective conjugate reduction of α,β-unsaturated esters with chiral phenol–carbene ligands
title_fullStr Copper-catalyzed enantioselective conjugate reduction of α,β-unsaturated esters with chiral phenol–carbene ligands
title_full_unstemmed Copper-catalyzed enantioselective conjugate reduction of α,β-unsaturated esters with chiral phenol–carbene ligands
title_short Copper-catalyzed enantioselective conjugate reduction of α,β-unsaturated esters with chiral phenol–carbene ligands
title_sort copper-catalyzed enantioselective conjugate reduction of α,β-unsaturated esters with chiral phenol–carbene ligands
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7136546/
https://www.ncbi.nlm.nih.gov/pubmed/32280383
http://dx.doi.org/10.3762/bjoc.16.50
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