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

Abstract 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...

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Autores principales:	Rui Guo, Qin Yang, Qinshan Tian, Guozhu Zhang
Formato:	article
Lenguaje:	EN
Publicado:	Nature Portfolio 2017
Materias:	Medicine R Science Q
Acceso en línea:	https://doaj.org/article/2dcb2202e31545a8a25fce3db2a4e609
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spelling	oai:doaj.org-article:2dcb2202e31545a8a25fce3db2a4e6092021-12-02T15:05:26ZBarbier-type anti-Diastereo- and Enantioselective Synthesis of β-Trimethylsilyl, Fluorinated Methyl, Phenylthio Homoallylic Alcohols10.1038/s41598-017-04986-x2045-2322https://doaj.org/article/2dcb2202e31545a8a25fce3db2a4e6092017-07-01T00:00:00Zhttps://doi.org/10.1038/s41598-017-04986-xhttps://doaj.org/toc/2045-2322Abstract 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.Rui GuoQin YangQinshan TianGuozhu ZhangNature PortfolioarticleMedicineRScienceQENScientific Reports, Vol 7, Iss 1, Pp 1-12 (2017)
institution	DOAJ
collection	DOAJ
language	EN
topic	Medicine R Science Q
spellingShingle	Medicine R Science Q Rui Guo Qin Yang Qinshan Tian Guozhu Zhang Barbier-type anti-Diastereo- and Enantioselective Synthesis of β-Trimethylsilyl, Fluorinated Methyl, Phenylthio Homoallylic Alcohols
description	Abstract 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.
format	article
author	Rui Guo Qin Yang Qinshan Tian Guozhu Zhang
author_facet	Rui Guo Qin Yang Qinshan Tian Guozhu Zhang
author_sort	Rui Guo
title	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_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_sort	barbier-type anti-diastereo- and enantioselective synthesis of β-trimethylsilyl, fluorinated methyl, phenylthio homoallylic alcohols
publisher	Nature Portfolio
publishDate	2017
url	https://doaj.org/article/2dcb2202e31545a8a25fce3db2a4e609
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Barbier-type anti-Diastereo- and Enantioselective Synthesis of β-Trimethylsilyl, Fluorinated Methyl, Phenylthio Homoallylic Alcohols

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