Preparation of Distant Quaternary Carbon Stereocenters by Double Selective Ring‐Opening of 1,1‐Biscyclopropyl Methanol Derivatives

The diastereoselective double carbometalation reaction of cyclopropenes provides, in a single‐pot operation, two ω‐ene‐[1,1]‐bicyclopropyl ester derivatives. One regioisomer then undergoes a Pd‐catalyzed addition of aryl iodide to provide skipped dienes possessing several distant stereocenters inclu...

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Detalles Bibliográficos
Autores principales: Siddaraju, Yogesh, Sabbatani, Juliette, Cohen, Anthony, Marek, Ilan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9401570/
https://www.ncbi.nlm.nih.gov/pubmed/35521738
http://dx.doi.org/10.1002/anie.202203652
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author Siddaraju, Yogesh
Sabbatani, Juliette
Cohen, Anthony
Marek, Ilan
author_facet Siddaraju, Yogesh
Sabbatani, Juliette
Cohen, Anthony
Marek, Ilan
author_sort Siddaraju, Yogesh
collection PubMed
description The diastereoselective double carbometalation reaction of cyclopropenes provides, in a single‐pot operation, two ω‐ene‐[1,1]‐bicyclopropyl ester derivatives. One regioisomer then undergoes a Pd‐catalyzed addition of aryl iodide to provide skipped dienes possessing several distant stereocenters including two congested quaternary carbon centers with excellent diastereoselectivity.
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spelling pubmed-94015702022-08-26 Preparation of Distant Quaternary Carbon Stereocenters by Double Selective Ring‐Opening of 1,1‐Biscyclopropyl Methanol Derivatives Siddaraju, Yogesh Sabbatani, Juliette Cohen, Anthony Marek, Ilan Angew Chem Int Ed Engl Communications The diastereoselective double carbometalation reaction of cyclopropenes provides, in a single‐pot operation, two ω‐ene‐[1,1]‐bicyclopropyl ester derivatives. One regioisomer then undergoes a Pd‐catalyzed addition of aryl iodide to provide skipped dienes possessing several distant stereocenters including two congested quaternary carbon centers with excellent diastereoselectivity. John Wiley and Sons Inc. 2022-05-20 2022-07-11 /pmc/articles/PMC9401570/ /pubmed/35521738 http://dx.doi.org/10.1002/anie.202203652 Text en © 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH https://creativecommons.org/licenses/by-nc-nd/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ (https://creativecommons.org/licenses/by-nc-nd/4.0/) License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Communications
Siddaraju, Yogesh
Sabbatani, Juliette
Cohen, Anthony
Marek, Ilan
Preparation of Distant Quaternary Carbon Stereocenters by Double Selective Ring‐Opening of 1,1‐Biscyclopropyl Methanol Derivatives
title Preparation of Distant Quaternary Carbon Stereocenters by Double Selective Ring‐Opening of 1,1‐Biscyclopropyl Methanol Derivatives
title_full Preparation of Distant Quaternary Carbon Stereocenters by Double Selective Ring‐Opening of 1,1‐Biscyclopropyl Methanol Derivatives
title_fullStr Preparation of Distant Quaternary Carbon Stereocenters by Double Selective Ring‐Opening of 1,1‐Biscyclopropyl Methanol Derivatives
title_full_unstemmed Preparation of Distant Quaternary Carbon Stereocenters by Double Selective Ring‐Opening of 1,1‐Biscyclopropyl Methanol Derivatives
title_short Preparation of Distant Quaternary Carbon Stereocenters by Double Selective Ring‐Opening of 1,1‐Biscyclopropyl Methanol Derivatives
title_sort preparation of distant quaternary carbon stereocenters by double selective ring‐opening of 1,1‐biscyclopropyl methanol derivatives
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9401570/
https://www.ncbi.nlm.nih.gov/pubmed/35521738
http://dx.doi.org/10.1002/anie.202203652
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