A General Diastereoselective Catalytic Vinylogous Aldol Reaction Among Tetramic Acid-Derived Pyrroles

[Image: see text] A catalytic diastereoselective aldol reaction has been developed for N1-arylated/C2-O-silylated/C3-methylated and brominated/C4-O-methylated pyrroles in its reactions with various aldehydes. Syn adducts emerge with regard to the vicinal nitrogen and oxygen heteroatom substituents....

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Autores principales: David, Jonathan G., Bai, Wen-Ju, Weaver, Marisa G., Pettus, Thomas R. R.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4156244/
https://www.ncbi.nlm.nih.gov/pubmed/25119431
http://dx.doi.org/10.1021/ol501715r
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author David, Jonathan G.
Bai, Wen-Ju
Weaver, Marisa G.
Pettus, Thomas R. R.
author_facet David, Jonathan G.
Bai, Wen-Ju
Weaver, Marisa G.
Pettus, Thomas R. R.
author_sort David, Jonathan G.
collection PubMed
description [Image: see text] A catalytic diastereoselective aldol reaction has been developed for N1-arylated/C2-O-silylated/C3-methylated and brominated/C4-O-methylated pyrroles in its reactions with various aldehydes. Syn adducts emerge with regard to the vicinal nitrogen and oxygen heteroatom substituents. The N1-aryl residue undergoes oxidative cleavage, and the C3-bromine atom undergoes palladium-mediated coupling reactions, both without disturbing the newly created stereocenters.
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spelling pubmed-41562442015-08-13 A General Diastereoselective Catalytic Vinylogous Aldol Reaction Among Tetramic Acid-Derived Pyrroles David, Jonathan G. Bai, Wen-Ju Weaver, Marisa G. Pettus, Thomas R. R. Org Lett [Image: see text] A catalytic diastereoselective aldol reaction has been developed for N1-arylated/C2-O-silylated/C3-methylated and brominated/C4-O-methylated pyrroles in its reactions with various aldehydes. Syn adducts emerge with regard to the vicinal nitrogen and oxygen heteroatom substituents. The N1-aryl residue undergoes oxidative cleavage, and the C3-bromine atom undergoes palladium-mediated coupling reactions, both without disturbing the newly created stereocenters. American Chemical Society 2014-08-13 2014-09-05 /pmc/articles/PMC4156244/ /pubmed/25119431 http://dx.doi.org/10.1021/ol501715r Text en Copyright © 2014 American Chemical Society Terms of Use (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html)
spellingShingle David, Jonathan G.
Bai, Wen-Ju
Weaver, Marisa G.
Pettus, Thomas R. R.
A General Diastereoselective Catalytic Vinylogous Aldol Reaction Among Tetramic Acid-Derived Pyrroles
title A General Diastereoselective Catalytic Vinylogous Aldol Reaction Among Tetramic Acid-Derived Pyrroles
title_full A General Diastereoselective Catalytic Vinylogous Aldol Reaction Among Tetramic Acid-Derived Pyrroles
title_fullStr A General Diastereoselective Catalytic Vinylogous Aldol Reaction Among Tetramic Acid-Derived Pyrroles
title_full_unstemmed A General Diastereoselective Catalytic Vinylogous Aldol Reaction Among Tetramic Acid-Derived Pyrroles
title_short A General Diastereoselective Catalytic Vinylogous Aldol Reaction Among Tetramic Acid-Derived Pyrroles
title_sort general diastereoselective catalytic vinylogous aldol reaction among tetramic acid-derived pyrroles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4156244/
https://www.ncbi.nlm.nih.gov/pubmed/25119431
http://dx.doi.org/10.1021/ol501715r
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