Gold and BINOL-Phosphoric Acid Catalyzed Enantioselective Hydroamination/N-Sulfonyliminium Cyclization Cascade

[Image: see text] A highly enantioselective hydroamination/N-sulfonyliminium cyclization cascade is reported using a combination of gold(I) and chiral phosphoric acid catalysts. An initial 5-exo-dig hydroamination and a subsequent phosphoric acid catalyzed cyclization process provide access to compl...

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Autores principales: Gregory, Alex W., Jakubec, Pavol, Turner, Paul, Dixon, Darren J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2013
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3931332/
https://www.ncbi.nlm.nih.gov/pubmed/23985045
http://dx.doi.org/10.1021/ol401784h
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author Gregory, Alex W.
Jakubec, Pavol
Turner, Paul
Dixon, Darren J.
author_facet Gregory, Alex W.
Jakubec, Pavol
Turner, Paul
Dixon, Darren J.
author_sort Gregory, Alex W.
collection PubMed
description [Image: see text] A highly enantioselective hydroamination/N-sulfonyliminium cyclization cascade is reported using a combination of gold(I) and chiral phosphoric acid catalysts. An initial 5-exo-dig hydroamination and a subsequent phosphoric acid catalyzed cyclization process provide access to complex sulfonamide scaffolds in excellent yield and high enantiocontrol. The method can be extended to lactam derivatives, with excellent yields and enantiomeric excesses of up to 93% ee.
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spelling pubmed-39313322014-02-21 Gold and BINOL-Phosphoric Acid Catalyzed Enantioselective Hydroamination/N-Sulfonyliminium Cyclization Cascade Gregory, Alex W. Jakubec, Pavol Turner, Paul Dixon, Darren J. Org Lett [Image: see text] A highly enantioselective hydroamination/N-sulfonyliminium cyclization cascade is reported using a combination of gold(I) and chiral phosphoric acid catalysts. An initial 5-exo-dig hydroamination and a subsequent phosphoric acid catalyzed cyclization process provide access to complex sulfonamide scaffolds in excellent yield and high enantiocontrol. The method can be extended to lactam derivatives, with excellent yields and enantiomeric excesses of up to 93% ee. American Chemical Society 2013-08-28 2013-09-06 /pmc/articles/PMC3931332/ /pubmed/23985045 http://dx.doi.org/10.1021/ol401784h Text en Copyright © 2013 American Chemical Society Terms of Use CC-BY (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html)
spellingShingle Gregory, Alex W.
Jakubec, Pavol
Turner, Paul
Dixon, Darren J.
Gold and BINOL-Phosphoric Acid Catalyzed Enantioselective Hydroamination/N-Sulfonyliminium Cyclization Cascade
title Gold and BINOL-Phosphoric Acid Catalyzed Enantioselective Hydroamination/N-Sulfonyliminium Cyclization Cascade
title_full Gold and BINOL-Phosphoric Acid Catalyzed Enantioselective Hydroamination/N-Sulfonyliminium Cyclization Cascade
title_fullStr Gold and BINOL-Phosphoric Acid Catalyzed Enantioselective Hydroamination/N-Sulfonyliminium Cyclization Cascade
title_full_unstemmed Gold and BINOL-Phosphoric Acid Catalyzed Enantioselective Hydroamination/N-Sulfonyliminium Cyclization Cascade
title_short Gold and BINOL-Phosphoric Acid Catalyzed Enantioselective Hydroamination/N-Sulfonyliminium Cyclization Cascade
title_sort gold and binol-phosphoric acid catalyzed enantioselective hydroamination/n-sulfonyliminium cyclization cascade
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3931332/
https://www.ncbi.nlm.nih.gov/pubmed/23985045
http://dx.doi.org/10.1021/ol401784h
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AT turnerpaul goldandbinolphosphoricacidcatalyzedenantioselectivehydroaminationnsulfonyliminiumcyclizationcascade
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