Rhodium‐Catalyzed Cyclization of Terminal and Internal Allenols: An Atom Economic and Highly Stereoselective Access Towards Tetrahydropyrans

A comprehensive study of a diastereoselective Rh‐catalyzed cyclization of terminal and internal allenols is reported. The methodology allows the atom economic and highly syn‐selective access to synthetically important 2,4‐disubstituted and 2,4,6‐trisubstituted tetrahydropyrans (THP). Furthermore, it...

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Autores principales: Schmidt, Johannes P., Breit, Bernhard
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/PMC7756761/
https://www.ncbi.nlm.nih.gov/pubmed/32940396
http://dx.doi.org/10.1002/anie.202009166
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author Schmidt, Johannes P.
Breit, Bernhard
author_facet Schmidt, Johannes P.
Breit, Bernhard
author_sort Schmidt, Johannes P.
collection PubMed
description A comprehensive study of a diastereoselective Rh‐catalyzed cyclization of terminal and internal allenols is reported. The methodology allows the atom economic and highly syn‐selective access to synthetically important 2,4‐disubstituted and 2,4,6‐trisubstituted tetrahydropyrans (THP). Furthermore, its utility and versatility are demonstrated by a great functional‐group compatibility and the enantioselective total synthesis of (−)‐centrolobine.
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spelling pubmed-77567612020-12-28 Rhodium‐Catalyzed Cyclization of Terminal and Internal Allenols: An Atom Economic and Highly Stereoselective Access Towards Tetrahydropyrans Schmidt, Johannes P. Breit, Bernhard Angew Chem Int Ed Engl Communications A comprehensive study of a diastereoselective Rh‐catalyzed cyclization of terminal and internal allenols is reported. The methodology allows the atom economic and highly syn‐selective access to synthetically important 2,4‐disubstituted and 2,4,6‐trisubstituted tetrahydropyrans (THP). Furthermore, its utility and versatility are demonstrated by a great functional‐group compatibility and the enantioselective total synthesis of (−)‐centrolobine. John Wiley and Sons Inc. 2020-10-26 2020-12-21 /pmc/articles/PMC7756761/ /pubmed/32940396 http://dx.doi.org/10.1002/anie.202009166 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/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Schmidt, Johannes P.
Breit, Bernhard
Rhodium‐Catalyzed Cyclization of Terminal and Internal Allenols: An Atom Economic and Highly Stereoselective Access Towards Tetrahydropyrans
title Rhodium‐Catalyzed Cyclization of Terminal and Internal Allenols: An Atom Economic and Highly Stereoselective Access Towards Tetrahydropyrans
title_full Rhodium‐Catalyzed Cyclization of Terminal and Internal Allenols: An Atom Economic and Highly Stereoselective Access Towards Tetrahydropyrans
title_fullStr Rhodium‐Catalyzed Cyclization of Terminal and Internal Allenols: An Atom Economic and Highly Stereoselective Access Towards Tetrahydropyrans
title_full_unstemmed Rhodium‐Catalyzed Cyclization of Terminal and Internal Allenols: An Atom Economic and Highly Stereoselective Access Towards Tetrahydropyrans
title_short Rhodium‐Catalyzed Cyclization of Terminal and Internal Allenols: An Atom Economic and Highly Stereoselective Access Towards Tetrahydropyrans
title_sort rhodium‐catalyzed cyclization of terminal and internal allenols: an atom economic and highly stereoselective access towards tetrahydropyrans
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7756761/
https://www.ncbi.nlm.nih.gov/pubmed/32940396
http://dx.doi.org/10.1002/anie.202009166
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