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1,2-Metallate Rearrangement as a Toolbox for the Synthesis of Allylic Alcohols
[Image: see text] The development of new methods and protocols for the synthesis of biologically active substances remains one of the most important pillars in organic chemistry, and one of these privileged structural motifs are allylic alcohols. The method of choice to date for the synthesis of the...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2023
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10476192/ https://www.ncbi.nlm.nih.gov/pubmed/37594929 http://dx.doi.org/10.1021/acs.joc.3c01309 |
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author | Linne, Yannick Lohrberg, Daniel Struwe, Henry Linne, Elvira Stohwasser, Anastasia Kalesse, Markus |
author_facet | Linne, Yannick Lohrberg, Daniel Struwe, Henry Linne, Elvira Stohwasser, Anastasia Kalesse, Markus |
author_sort | Linne, Yannick |
collection | PubMed |
description | [Image: see text] The development of new methods and protocols for the synthesis of biologically active substances remains one of the most important pillars in organic chemistry, and one of these privileged structural motifs are allylic alcohols. The method of choice to date for the synthesis of these is the Nozaki–Hiyama–Takai–Kishi reaction. We describe here a valuable alternative to the synthesis of allylic alcohols via 1,2-metallate rearrangement. In this work, various vinyl boronic esters with different functional groups have been applied in the Hoppe–Matteson–Aggarwal reaction. In addition, two monoterpenoids were constructed via this convergent synthetic strategy. |
format | Online Article Text |
id | pubmed-10476192 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-104761922023-09-05 1,2-Metallate Rearrangement as a Toolbox for the Synthesis of Allylic Alcohols Linne, Yannick Lohrberg, Daniel Struwe, Henry Linne, Elvira Stohwasser, Anastasia Kalesse, Markus J Org Chem [Image: see text] The development of new methods and protocols for the synthesis of biologically active substances remains one of the most important pillars in organic chemistry, and one of these privileged structural motifs are allylic alcohols. The method of choice to date for the synthesis of these is the Nozaki–Hiyama–Takai–Kishi reaction. We describe here a valuable alternative to the synthesis of allylic alcohols via 1,2-metallate rearrangement. In this work, various vinyl boronic esters with different functional groups have been applied in the Hoppe–Matteson–Aggarwal reaction. In addition, two monoterpenoids were constructed via this convergent synthetic strategy. American Chemical Society 2023-08-18 /pmc/articles/PMC10476192/ /pubmed/37594929 http://dx.doi.org/10.1021/acs.joc.3c01309 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Linne, Yannick Lohrberg, Daniel Struwe, Henry Linne, Elvira Stohwasser, Anastasia Kalesse, Markus 1,2-Metallate Rearrangement as a Toolbox for the Synthesis of Allylic Alcohols |
title | 1,2-Metallate Rearrangement
as a Toolbox for the Synthesis
of Allylic Alcohols |
title_full | 1,2-Metallate Rearrangement
as a Toolbox for the Synthesis
of Allylic Alcohols |
title_fullStr | 1,2-Metallate Rearrangement
as a Toolbox for the Synthesis
of Allylic Alcohols |
title_full_unstemmed | 1,2-Metallate Rearrangement
as a Toolbox for the Synthesis
of Allylic Alcohols |
title_short | 1,2-Metallate Rearrangement
as a Toolbox for the Synthesis
of Allylic Alcohols |
title_sort | 1,2-metallate rearrangement
as a toolbox for the synthesis
of allylic alcohols |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10476192/ https://www.ncbi.nlm.nih.gov/pubmed/37594929 http://dx.doi.org/10.1021/acs.joc.3c01309 |
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