Desymmetrization of meso-Dibromocycloalkenes through Copper(I)-Catalyzed Asymmetric Allylic Substitution with Organolithium Reagents

[Image: see text] The highly regio- and enantioselective (up to >99:1 dr, up to 99:1 er) desymmetrization of meso-1,4-dibromocycloalk-2-enes using asymmetric allylic substitution with organolithium reagents to afford enantioenriched bromocycloalkenes (ring size of 5 to 7) has been achieved. The c...

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Autores principales: Goh, Shermin S., Guduguntla, Sureshbabu, Kikuchi, Takashi, Lutz, Martin, Otten, Edwin, Fujita, Makoto, Feringa, Ben L.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2018
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6002767/
https://www.ncbi.nlm.nih.gov/pubmed/29790736
http://dx.doi.org/10.1021/jacs.8b02992
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author Goh, Shermin S.
Guduguntla, Sureshbabu
Kikuchi, Takashi
Lutz, Martin
Otten, Edwin
Fujita, Makoto
Feringa, Ben L.
author_facet Goh, Shermin S.
Guduguntla, Sureshbabu
Kikuchi, Takashi
Lutz, Martin
Otten, Edwin
Fujita, Makoto
Feringa, Ben L.
author_sort Goh, Shermin S.
collection PubMed
description [Image: see text] The highly regio- and enantioselective (up to >99:1 dr, up to 99:1 er) desymmetrization of meso-1,4-dibromocycloalk-2-enes using asymmetric allylic substitution with organolithium reagents to afford enantioenriched bromocycloalkenes (ring size of 5 to 7) has been achieved. The cycloheptene products undergo an unusual ring contraction. The synthetic versatility of this Cu(I)-catalyzed reaction is demonstrated by the concise stereocontrolled preparation of cyclic amino alcohols, which are privileged chiral structures in natural products and pharmaceuticals and widely used in synthesis and catalysis.
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spelling pubmed-60027672018-06-19 Desymmetrization of meso-Dibromocycloalkenes through Copper(I)-Catalyzed Asymmetric Allylic Substitution with Organolithium Reagents Goh, Shermin S. Guduguntla, Sureshbabu Kikuchi, Takashi Lutz, Martin Otten, Edwin Fujita, Makoto Feringa, Ben L. J Am Chem Soc [Image: see text] The highly regio- and enantioselective (up to >99:1 dr, up to 99:1 er) desymmetrization of meso-1,4-dibromocycloalk-2-enes using asymmetric allylic substitution with organolithium reagents to afford enantioenriched bromocycloalkenes (ring size of 5 to 7) has been achieved. The cycloheptene products undergo an unusual ring contraction. The synthetic versatility of this Cu(I)-catalyzed reaction is demonstrated by the concise stereocontrolled preparation of cyclic amino alcohols, which are privileged chiral structures in natural products and pharmaceuticals and widely used in synthesis and catalysis. American Chemical Society 2018-05-23 2018-06-13 /pmc/articles/PMC6002767/ /pubmed/29790736 http://dx.doi.org/10.1021/jacs.8b02992 Text en Copyright © 2018 American Chemical Society This is an open access article published under a Creative Commons Non-Commercial No Derivative Works (CC-BY-NC-ND) Attribution License (http://pubs.acs.org/page/policy/authorchoice_ccbyncnd_termsofuse.html) , which permits copying and redistribution of the article, and creation of adaptations, all for non-commercial purposes.
spellingShingle Goh, Shermin S.
Guduguntla, Sureshbabu
Kikuchi, Takashi
Lutz, Martin
Otten, Edwin
Fujita, Makoto
Feringa, Ben L.
Desymmetrization of meso-Dibromocycloalkenes through Copper(I)-Catalyzed Asymmetric Allylic Substitution with Organolithium Reagents
title Desymmetrization of meso-Dibromocycloalkenes through Copper(I)-Catalyzed Asymmetric Allylic Substitution with Organolithium Reagents
title_full Desymmetrization of meso-Dibromocycloalkenes through Copper(I)-Catalyzed Asymmetric Allylic Substitution with Organolithium Reagents
title_fullStr Desymmetrization of meso-Dibromocycloalkenes through Copper(I)-Catalyzed Asymmetric Allylic Substitution with Organolithium Reagents
title_full_unstemmed Desymmetrization of meso-Dibromocycloalkenes through Copper(I)-Catalyzed Asymmetric Allylic Substitution with Organolithium Reagents
title_short Desymmetrization of meso-Dibromocycloalkenes through Copper(I)-Catalyzed Asymmetric Allylic Substitution with Organolithium Reagents
title_sort desymmetrization of meso-dibromocycloalkenes through copper(i)-catalyzed asymmetric allylic substitution with organolithium reagents
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6002767/
https://www.ncbi.nlm.nih.gov/pubmed/29790736
http://dx.doi.org/10.1021/jacs.8b02992
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