Enantioselective Michael Addition/Iminium Ion Cyclization Cascades of Tryptamine-Derived Ureas

[Image: see text] A Michael addition/iminium ion cyclization cascade of enones with tryptamine-derived ureas under BINOL phosphoric acid (BPA) catalysis is reported. The cascade reaction tolerates a wide variety of easily synthesized tryptamine-derived ureas, including those bearing substituents on...

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Autores principales: Aillaud, Isabelle, Barber, David M., Thompson, Amber L., 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/PMC3931331/
https://www.ncbi.nlm.nih.gov/pubmed/23721179
http://dx.doi.org/10.1021/ol401039h
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author Aillaud, Isabelle
Barber, David M.
Thompson, Amber L.
Dixon, Darren J.
author_facet Aillaud, Isabelle
Barber, David M.
Thompson, Amber L.
Dixon, Darren J.
author_sort Aillaud, Isabelle
collection PubMed
description [Image: see text] A Michael addition/iminium ion cyclization cascade of enones with tryptamine-derived ureas under BINOL phosphoric acid (BPA) catalysis is reported. The cascade reaction tolerates a wide variety of easily synthesized tryptamine-derived ureas, including those bearing substituents on the distal nitrogen atom of the urea moiety, affording polyheterocyclic products in good yields and good to excellent enantioselectivities.
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spelling pubmed-39313312014-02-21 Enantioselective Michael Addition/Iminium Ion Cyclization Cascades of Tryptamine-Derived Ureas Aillaud, Isabelle Barber, David M. Thompson, Amber L. Dixon, Darren J. Org Lett [Image: see text] A Michael addition/iminium ion cyclization cascade of enones with tryptamine-derived ureas under BINOL phosphoric acid (BPA) catalysis is reported. The cascade reaction tolerates a wide variety of easily synthesized tryptamine-derived ureas, including those bearing substituents on the distal nitrogen atom of the urea moiety, affording polyheterocyclic products in good yields and good to excellent enantioselectivities. American Chemical Society 2013-05-30 2013-06-21 /pmc/articles/PMC3931331/ /pubmed/23721179 http://dx.doi.org/10.1021/ol401039h Text en Copyright © 2013 American Chemical Society Terms of Use CC-BY (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html)
spellingShingle Aillaud, Isabelle
Barber, David M.
Thompson, Amber L.
Dixon, Darren J.
Enantioselective Michael Addition/Iminium Ion Cyclization Cascades of Tryptamine-Derived Ureas
title Enantioselective Michael Addition/Iminium Ion Cyclization Cascades of Tryptamine-Derived Ureas
title_full Enantioselective Michael Addition/Iminium Ion Cyclization Cascades of Tryptamine-Derived Ureas
title_fullStr Enantioselective Michael Addition/Iminium Ion Cyclization Cascades of Tryptamine-Derived Ureas
title_full_unstemmed Enantioselective Michael Addition/Iminium Ion Cyclization Cascades of Tryptamine-Derived Ureas
title_short Enantioselective Michael Addition/Iminium Ion Cyclization Cascades of Tryptamine-Derived Ureas
title_sort enantioselective michael addition/iminium ion cyclization cascades of tryptamine-derived ureas
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3931331/
https://www.ncbi.nlm.nih.gov/pubmed/23721179
http://dx.doi.org/10.1021/ol401039h
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