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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...

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Autores principales: Linne, Yannick, Lohrberg, Daniel, Struwe, Henry, Linne, Elvira, Stohwasser, Anastasia, Kalesse, Markus
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
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.
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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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