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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...

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Detalles Bibliográficos
Autores principales: Ghosh, Santanu, Das, Sayantani, De, Chandra Kanta, Yepes, Diana, Neese, Frank, Bistoni, Giovanni, Leutzsch, Markus, List, Benjamin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
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.
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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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