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Strong and Confined Acids Control Five Stereogenic Centers in Catalytic Asymmetric Diels–Alder Reactions of Cyclohexadienones with Cyclopentadiene
We describe a highly enantioselective Diels–Alder reaction of cross‐conjugated cyclohexadienones with cyclopentadiene, in which five stereocenters are effectively controlled by a strongly acidic and confined imidodiphosphorimidate catalyst. Our approach provides tricyclic products in excellent stere...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7383742/ https://www.ncbi.nlm.nih.gov/pubmed/32159921 http://dx.doi.org/10.1002/anie.202000307 |
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author | Ghosh, Santanu Das, Sayantani De, Chandra Kanta Yepes, Diana Neese, Frank Bistoni, Giovanni Leutzsch, Markus List, Benjamin |
author_facet | Ghosh, Santanu Das, Sayantani De, Chandra Kanta Yepes, Diana Neese, Frank Bistoni, Giovanni Leutzsch, Markus List, Benjamin |
author_sort | Ghosh, Santanu |
collection | PubMed |
description | We describe a highly enantioselective Diels–Alder reaction of cross‐conjugated cyclohexadienones with cyclopentadiene, in which five stereocenters are effectively controlled by a strongly acidic and confined imidodiphosphorimidate catalyst. Our approach provides tricyclic products in excellent stereoselectivity. We also report methods to convert the obtained products into useful intermediates and a computational study that aids in gaining deeper insight into the reaction mechanism and origin of stereoselectivity. |
format | Online Article Text |
id | pubmed-7383742 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-73837422020-07-27 Strong and Confined Acids Control Five Stereogenic Centers in Catalytic Asymmetric Diels–Alder Reactions of Cyclohexadienones with Cyclopentadiene Ghosh, Santanu Das, Sayantani De, Chandra Kanta Yepes, Diana Neese, Frank Bistoni, Giovanni Leutzsch, Markus List, Benjamin Angew Chem Int Ed Engl Communications We describe a highly enantioselective Diels–Alder reaction of cross‐conjugated cyclohexadienones with cyclopentadiene, in which five stereocenters are effectively controlled by a strongly acidic and confined imidodiphosphorimidate catalyst. Our approach provides tricyclic products in excellent stereoselectivity. We also report methods to convert the obtained products into useful intermediates and a computational study that aids in gaining deeper insight into the reaction mechanism and origin of stereoselectivity. John Wiley and Sons Inc. 2020-03-11 2020-07-20 /pmc/articles/PMC7383742/ /pubmed/32159921 http://dx.doi.org/10.1002/anie.202000307 Text en © 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. |
spellingShingle | Communications Ghosh, Santanu Das, Sayantani De, Chandra Kanta Yepes, Diana Neese, Frank Bistoni, Giovanni Leutzsch, Markus List, Benjamin Strong and Confined Acids Control Five Stereogenic Centers in Catalytic Asymmetric Diels–Alder Reactions of Cyclohexadienones with Cyclopentadiene |
title | Strong and Confined Acids Control Five Stereogenic Centers in Catalytic Asymmetric Diels–Alder Reactions of Cyclohexadienones with Cyclopentadiene |
title_full | Strong and Confined Acids Control Five Stereogenic Centers in Catalytic Asymmetric Diels–Alder Reactions of Cyclohexadienones with Cyclopentadiene |
title_fullStr | Strong and Confined Acids Control Five Stereogenic Centers in Catalytic Asymmetric Diels–Alder Reactions of Cyclohexadienones with Cyclopentadiene |
title_full_unstemmed | Strong and Confined Acids Control Five Stereogenic Centers in Catalytic Asymmetric Diels–Alder Reactions of Cyclohexadienones with Cyclopentadiene |
title_short | Strong and Confined Acids Control Five Stereogenic Centers in Catalytic Asymmetric Diels–Alder Reactions of Cyclohexadienones with Cyclopentadiene |
title_sort | strong and confined acids control five stereogenic centers in catalytic asymmetric diels–alder reactions of cyclohexadienones with cyclopentadiene |
topic | Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7383742/ https://www.ncbi.nlm.nih.gov/pubmed/32159921 http://dx.doi.org/10.1002/anie.202000307 |
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