Thiourea-Catalyzed Enantioselective Addition of Indoles to Pyrones: Alkaloid Cores with Quaternary Carbons

[Image: see text] We report the development of a catalytic method for the enantioselective addition of indoles to pyrone-derived electrophiles. Arylpyrrolidino-derived thioureas catalyze the addition with high stereoselectivity in the presence of catalytic quantities of an achiral Brønsted acid. The...

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Autores principales: Yeung, Charles S., Ziegler, Robert E., Porco, John A., Jacobsen, Eric N.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4235369/
https://www.ncbi.nlm.nih.gov/pubmed/25213353
http://dx.doi.org/10.1021/ja508523g
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author Yeung, Charles S.
Ziegler, Robert E.
Porco, John A.
Jacobsen, Eric N.
author_facet Yeung, Charles S.
Ziegler, Robert E.
Porco, John A.
Jacobsen, Eric N.
author_sort Yeung, Charles S.
collection PubMed
description [Image: see text] We report the development of a catalytic method for the enantioselective addition of indoles to pyrone-derived electrophiles. Arylpyrrolidino-derived thioureas catalyze the addition with high stereoselectivity in the presence of catalytic quantities of an achiral Brønsted acid. The indole–pyrone adducts feature a quaternary stereocenter and represent an unusual class of indolines bearing structural resemblance to the hybrid natural product pleiocarpamine.
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spelling pubmed-42353692015-09-12 Thiourea-Catalyzed Enantioselective Addition of Indoles to Pyrones: Alkaloid Cores with Quaternary Carbons Yeung, Charles S. Ziegler, Robert E. Porco, John A. Jacobsen, Eric N. J Am Chem Soc [Image: see text] We report the development of a catalytic method for the enantioselective addition of indoles to pyrone-derived electrophiles. Arylpyrrolidino-derived thioureas catalyze the addition with high stereoselectivity in the presence of catalytic quantities of an achiral Brønsted acid. The indole–pyrone adducts feature a quaternary stereocenter and represent an unusual class of indolines bearing structural resemblance to the hybrid natural product pleiocarpamine. American Chemical Society 2014-09-12 2014-10-01 /pmc/articles/PMC4235369/ /pubmed/25213353 http://dx.doi.org/10.1021/ja508523g 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 Yeung, Charles S.
Ziegler, Robert E.
Porco, John A.
Jacobsen, Eric N.
Thiourea-Catalyzed Enantioselective Addition of Indoles to Pyrones: Alkaloid Cores with Quaternary Carbons
title Thiourea-Catalyzed Enantioselective Addition of Indoles to Pyrones: Alkaloid Cores with Quaternary Carbons
title_full Thiourea-Catalyzed Enantioselective Addition of Indoles to Pyrones: Alkaloid Cores with Quaternary Carbons
title_fullStr Thiourea-Catalyzed Enantioselective Addition of Indoles to Pyrones: Alkaloid Cores with Quaternary Carbons
title_full_unstemmed Thiourea-Catalyzed Enantioselective Addition of Indoles to Pyrones: Alkaloid Cores with Quaternary Carbons
title_short Thiourea-Catalyzed Enantioselective Addition of Indoles to Pyrones: Alkaloid Cores with Quaternary Carbons
title_sort thiourea-catalyzed enantioselective addition of indoles to pyrones: alkaloid cores with quaternary carbons
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4235369/
https://www.ncbi.nlm.nih.gov/pubmed/25213353
http://dx.doi.org/10.1021/ja508523g
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AT porcojohna thioureacatalyzedenantioselectiveadditionofindolestopyronesalkaloidcoreswithquaternarycarbons
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