A New Entry to Azomethine Ylides from Allylic Amines and Glyoxals: Shifting the Reliance on Amino Ester Precursors

[Image: see text] The first examples of azomethine ylides derived from allylic amine and glyoxal precursors are reported. The condensation of primary allylic and α-aryl amines with glyoxylates or α-aryl glyoxals affords conjugated azomethine ylides that undergo facile [3 + 2] cycloaddition, providin...

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Autores principales: Machamer, Natalie K., Liu, Xiaoxi, Waters, Stephen P.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4184444/
https://www.ncbi.nlm.nih.gov/pubmed/25247255
http://dx.doi.org/10.1021/ol5022614
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author Machamer, Natalie K.
Liu, Xiaoxi
Waters, Stephen P.
author_facet Machamer, Natalie K.
Liu, Xiaoxi
Waters, Stephen P.
author_sort Machamer, Natalie K.
collection PubMed
description [Image: see text] The first examples of azomethine ylides derived from allylic amine and glyoxal precursors are reported. The condensation of primary allylic and α-aryl amines with glyoxylates or α-aryl glyoxals affords conjugated azomethine ylides that undergo facile [3 + 2] cycloaddition, providing 5-alkenyl pyrrolidine cycloadducts that cannot be accessed through the classical use of amino esters as ylide precursors.
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spelling pubmed-41844442015-09-23 A New Entry to Azomethine Ylides from Allylic Amines and Glyoxals: Shifting the Reliance on Amino Ester Precursors Machamer, Natalie K. Liu, Xiaoxi Waters, Stephen P. Org Lett [Image: see text] The first examples of azomethine ylides derived from allylic amine and glyoxal precursors are reported. The condensation of primary allylic and α-aryl amines with glyoxylates or α-aryl glyoxals affords conjugated azomethine ylides that undergo facile [3 + 2] cycloaddition, providing 5-alkenyl pyrrolidine cycloadducts that cannot be accessed through the classical use of amino esters as ylide precursors. American Chemical Society 2014-09-23 2014-10-03 /pmc/articles/PMC4184444/ /pubmed/25247255 http://dx.doi.org/10.1021/ol5022614 Text en Copyright © 2014 American Chemical Society Terms of Use (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html)
spellingShingle Machamer, Natalie K.
Liu, Xiaoxi
Waters, Stephen P.
A New Entry to Azomethine Ylides from Allylic Amines and Glyoxals: Shifting the Reliance on Amino Ester Precursors
title A New Entry to Azomethine Ylides from Allylic Amines and Glyoxals: Shifting the Reliance on Amino Ester Precursors
title_full A New Entry to Azomethine Ylides from Allylic Amines and Glyoxals: Shifting the Reliance on Amino Ester Precursors
title_fullStr A New Entry to Azomethine Ylides from Allylic Amines and Glyoxals: Shifting the Reliance on Amino Ester Precursors
title_full_unstemmed A New Entry to Azomethine Ylides from Allylic Amines and Glyoxals: Shifting the Reliance on Amino Ester Precursors
title_short A New Entry to Azomethine Ylides from Allylic Amines and Glyoxals: Shifting the Reliance on Amino Ester Precursors
title_sort new entry to azomethine ylides from allylic amines and glyoxals: shifting the reliance on amino ester precursors
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4184444/
https://www.ncbi.nlm.nih.gov/pubmed/25247255
http://dx.doi.org/10.1021/ol5022614
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