The Cyclohexa‐2,5‐dienyl Group as a Placeholder for Hydrogen: Organocatalytic Michael Addition of an Acetaldehyde Surrogate

An aldehyde with a cyclohexa‐2,5‐dienyl group in the α‐position is introduced as a storable surrogate of highly reactive acetaldehyde. The cyclohexa‐2,5‐dienyl unit is compatible with an enantioselective Michael addition to nitroalkenes promoted by a Hayashi–Jørgensen catalyst and can be removed by...

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Detalles Bibliográficos
Autores principales: Chen, Weiqiang, Fang, Huaquan, Xie, Kaixue, Oestreich, Martin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7756304/
https://www.ncbi.nlm.nih.gov/pubmed/32808731
http://dx.doi.org/10.1002/chem.202003764
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author Chen, Weiqiang
Fang, Huaquan
Xie, Kaixue
Oestreich, Martin
author_facet Chen, Weiqiang
Fang, Huaquan
Xie, Kaixue
Oestreich, Martin
author_sort Chen, Weiqiang
collection PubMed
description An aldehyde with a cyclohexa‐2,5‐dienyl group in the α‐position is introduced as a storable surrogate of highly reactive acetaldehyde. The cyclohexa‐2,5‐dienyl unit is compatible with an enantioselective Michael addition to nitroalkenes promoted by a Hayashi–Jørgensen catalyst and can be removed by a boron Lewis acid mediated C−C bond cleavage. The robust two‐step sequence does not require a large excess of the aldehyde component that is typically needed when directly using acetaldehyde.
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spelling pubmed-77563042020-12-28 The Cyclohexa‐2,5‐dienyl Group as a Placeholder for Hydrogen: Organocatalytic Michael Addition of an Acetaldehyde Surrogate Chen, Weiqiang Fang, Huaquan Xie, Kaixue Oestreich, Martin Chemistry Communications An aldehyde with a cyclohexa‐2,5‐dienyl group in the α‐position is introduced as a storable surrogate of highly reactive acetaldehyde. The cyclohexa‐2,5‐dienyl unit is compatible with an enantioselective Michael addition to nitroalkenes promoted by a Hayashi–Jørgensen catalyst and can be removed by a boron Lewis acid mediated C−C bond cleavage. The robust two‐step sequence does not require a large excess of the aldehyde component that is typically needed when directly using acetaldehyde. John Wiley and Sons Inc. 2020-10-22 2020-11-26 /pmc/articles/PMC7756304/ /pubmed/32808731 http://dx.doi.org/10.1002/chem.202003764 Text en © 2020 The Authors. Published by Wiley-VCH GmbH This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes.
spellingShingle Communications
Chen, Weiqiang
Fang, Huaquan
Xie, Kaixue
Oestreich, Martin
The Cyclohexa‐2,5‐dienyl Group as a Placeholder for Hydrogen: Organocatalytic Michael Addition of an Acetaldehyde Surrogate
title The Cyclohexa‐2,5‐dienyl Group as a Placeholder for Hydrogen: Organocatalytic Michael Addition of an Acetaldehyde Surrogate
title_full The Cyclohexa‐2,5‐dienyl Group as a Placeholder for Hydrogen: Organocatalytic Michael Addition of an Acetaldehyde Surrogate
title_fullStr The Cyclohexa‐2,5‐dienyl Group as a Placeholder for Hydrogen: Organocatalytic Michael Addition of an Acetaldehyde Surrogate
title_full_unstemmed The Cyclohexa‐2,5‐dienyl Group as a Placeholder for Hydrogen: Organocatalytic Michael Addition of an Acetaldehyde Surrogate
title_short The Cyclohexa‐2,5‐dienyl Group as a Placeholder for Hydrogen: Organocatalytic Michael Addition of an Acetaldehyde Surrogate
title_sort cyclohexa‐2,5‐dienyl group as a placeholder for hydrogen: organocatalytic michael addition of an acetaldehyde surrogate
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7756304/
https://www.ncbi.nlm.nih.gov/pubmed/32808731
http://dx.doi.org/10.1002/chem.202003764
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