Asymmetric Synthesis of First Generation Molecular Motors

[Image: see text] A general enantioselective route to functionalized first generation molecular motors is described. An enantioselective protonation of the silyl enol ethers of indanones by a Au(I)BINAP complex sets the stage for a highly diastereoselective McMurry coupling as a second enhancement s...

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Autores principales: Neubauer, Thomas M., van Leeuwen, Thomas, Zhao, Depeng, Lubbe, Anouk S., Kistemaker, Jos C. M., Feringa, Ben L.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5055213/
https://www.ncbi.nlm.nih.gov/pubmed/25079823
http://dx.doi.org/10.1021/ol501925f
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author Neubauer, Thomas M.
van Leeuwen, Thomas
Zhao, Depeng
Lubbe, Anouk S.
Kistemaker, Jos C. M.
Feringa, Ben L.
author_facet Neubauer, Thomas M.
van Leeuwen, Thomas
Zhao, Depeng
Lubbe, Anouk S.
Kistemaker, Jos C. M.
Feringa, Ben L.
author_sort Neubauer, Thomas M.
collection PubMed
description [Image: see text] A general enantioselective route to functionalized first generation molecular motors is described. An enantioselective protonation of the silyl enol ethers of indanones by a Au(I)BINAP complex sets the stage for a highly diastereoselective McMurry coupling as a second enhancement step for enantiomeric excess. In this way various functionalized overcrowded alkenes could be synthesized in good yields (up to 78%) and good to excellent enantiomeric excess (85% ee–>98% ee) values.
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spelling pubmed-50552132016-10-10 Asymmetric Synthesis of First Generation Molecular Motors Neubauer, Thomas M. van Leeuwen, Thomas Zhao, Depeng Lubbe, Anouk S. Kistemaker, Jos C. M. Feringa, Ben L. Org Lett [Image: see text] A general enantioselective route to functionalized first generation molecular motors is described. An enantioselective protonation of the silyl enol ethers of indanones by a Au(I)BINAP complex sets the stage for a highly diastereoselective McMurry coupling as a second enhancement step for enantiomeric excess. In this way various functionalized overcrowded alkenes could be synthesized in good yields (up to 78%) and good to excellent enantiomeric excess (85% ee–>98% ee) values. American Chemical Society 2014-07-31 2014-08-15 /pmc/articles/PMC5055213/ /pubmed/25079823 http://dx.doi.org/10.1021/ol501925f Text en Copyright © 2014 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Neubauer, Thomas M.
van Leeuwen, Thomas
Zhao, Depeng
Lubbe, Anouk S.
Kistemaker, Jos C. M.
Feringa, Ben L.
Asymmetric Synthesis of First Generation Molecular Motors
title Asymmetric Synthesis of First Generation Molecular Motors
title_full Asymmetric Synthesis of First Generation Molecular Motors
title_fullStr Asymmetric Synthesis of First Generation Molecular Motors
title_full_unstemmed Asymmetric Synthesis of First Generation Molecular Motors
title_short Asymmetric Synthesis of First Generation Molecular Motors
title_sort asymmetric synthesis of first generation molecular motors
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5055213/
https://www.ncbi.nlm.nih.gov/pubmed/25079823
http://dx.doi.org/10.1021/ol501925f
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