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Barbier-type anti-Diastereo- and Enantioselective Synthesis of β-Trimethylsilyl, Fluorinated Methyl, Phenylthio Homoallylic Alcohols

Catalytic Asymmetric allylation of aldehydes with functionalized allylic reagents represents an important process in synthetic organic chemistry because the resulting chiral homoallylic alcohols are valuable building blocks in diverse research fields. Despite the obvious advantages of allyl halides...

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Autores principales: Guo, Rui, Yang, Qin, Tian, Qinshan, Zhang, Guozhu
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5501818/
https://www.ncbi.nlm.nih.gov/pubmed/28687768
http://dx.doi.org/10.1038/s41598-017-04986-x
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author Guo, Rui
Yang, Qin
Tian, Qinshan
Zhang, Guozhu
author_facet Guo, Rui
Yang, Qin
Tian, Qinshan
Zhang, Guozhu
author_sort Guo, Rui
collection PubMed
description Catalytic Asymmetric allylation of aldehydes with functionalized allylic reagents represents an important process in synthetic organic chemistry because the resulting chiral homoallylic alcohols are valuable building blocks in diverse research fields. Despite the obvious advantages of allyl halides as allylation reagent under Barbier-type conditions, catalytic asymmetric version using functionalized allyl halides remains largely underdeveloped. Here, we addressed this issue by employing a chromium-catalysis system. The use of readily available allyl bromides with γ substitutions including trimethylsilyl, fluorinated methyl and phenylthio groups provided an efficient and convenient method to introduce those privileged functionalities into homoallylic alcohols. Good yields, high anti-diastereo- and excellent enantioselectivities were achieved under mild reaction conditions.
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spelling pubmed-55018182017-07-10 Barbier-type anti-Diastereo- and Enantioselective Synthesis of β-Trimethylsilyl, Fluorinated Methyl, Phenylthio Homoallylic Alcohols Guo, Rui Yang, Qin Tian, Qinshan Zhang, Guozhu Sci Rep Article Catalytic Asymmetric allylation of aldehydes with functionalized allylic reagents represents an important process in synthetic organic chemistry because the resulting chiral homoallylic alcohols are valuable building blocks in diverse research fields. Despite the obvious advantages of allyl halides as allylation reagent under Barbier-type conditions, catalytic asymmetric version using functionalized allyl halides remains largely underdeveloped. Here, we addressed this issue by employing a chromium-catalysis system. The use of readily available allyl bromides with γ substitutions including trimethylsilyl, fluorinated methyl and phenylthio groups provided an efficient and convenient method to introduce those privileged functionalities into homoallylic alcohols. Good yields, high anti-diastereo- and excellent enantioselectivities were achieved under mild reaction conditions. Nature Publishing Group UK 2017-07-07 /pmc/articles/PMC5501818/ /pubmed/28687768 http://dx.doi.org/10.1038/s41598-017-04986-x Text en © The Author(s) 2017 Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.
spellingShingle Article
Guo, Rui
Yang, Qin
Tian, Qinshan
Zhang, Guozhu
Barbier-type anti-Diastereo- and Enantioselective Synthesis of β-Trimethylsilyl, Fluorinated Methyl, Phenylthio Homoallylic Alcohols
title Barbier-type anti-Diastereo- and Enantioselective Synthesis of β-Trimethylsilyl, Fluorinated Methyl, Phenylthio Homoallylic Alcohols
title_full Barbier-type anti-Diastereo- and Enantioselective Synthesis of β-Trimethylsilyl, Fluorinated Methyl, Phenylthio Homoallylic Alcohols
title_fullStr Barbier-type anti-Diastereo- and Enantioselective Synthesis of β-Trimethylsilyl, Fluorinated Methyl, Phenylthio Homoallylic Alcohols
title_full_unstemmed Barbier-type anti-Diastereo- and Enantioselective Synthesis of β-Trimethylsilyl, Fluorinated Methyl, Phenylthio Homoallylic Alcohols
title_short Barbier-type anti-Diastereo- and Enantioselective Synthesis of β-Trimethylsilyl, Fluorinated Methyl, Phenylthio Homoallylic Alcohols
title_sort barbier-type anti-diastereo- and enantioselective synthesis of β-trimethylsilyl, fluorinated methyl, phenylthio homoallylic alcohols
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5501818/
https://www.ncbi.nlm.nih.gov/pubmed/28687768
http://dx.doi.org/10.1038/s41598-017-04986-x
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