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Gold-catalyzed cyclization of allenyl acetal derivatives
The gold-catalyzed transformation of allenyl acetals into 5-alkylidenecyclopent-2-en-1-ones is described. The outcome of our deuterium labeling experiments supports a 1,4-hydride shift of the resulting allyl cationic intermediates because a complete deuterium transfer is observed. We tested the reac...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Beilstein-Institut
2013
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3778408/ https://www.ncbi.nlm.nih.gov/pubmed/24062838 http://dx.doi.org/10.3762/bjoc.9.202 |
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author | Vasu, Dhananjayan Pawar, Samir Kundlik Liu, Rai-Shung |
author_facet | Vasu, Dhananjayan Pawar, Samir Kundlik Liu, Rai-Shung |
author_sort | Vasu, Dhananjayan |
collection | PubMed |
description | The gold-catalyzed transformation of allenyl acetals into 5-alkylidenecyclopent-2-en-1-ones is described. The outcome of our deuterium labeling experiments supports a 1,4-hydride shift of the resulting allyl cationic intermediates because a complete deuterium transfer is observed. We tested the reaction on various acetal substrates bearing a propargyl acetate, giving 4-methoxy-5-alkylidenecyclopent-2-en-1-ones 4 via a degradation of the acetate group at the allyl cation intermediate. |
format | Online Article Text |
id | pubmed-3778408 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2013 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
spelling | pubmed-37784082013-09-23 Gold-catalyzed cyclization of allenyl acetal derivatives Vasu, Dhananjayan Pawar, Samir Kundlik Liu, Rai-Shung Beilstein J Org Chem Full Research Paper The gold-catalyzed transformation of allenyl acetals into 5-alkylidenecyclopent-2-en-1-ones is described. The outcome of our deuterium labeling experiments supports a 1,4-hydride shift of the resulting allyl cationic intermediates because a complete deuterium transfer is observed. We tested the reaction on various acetal substrates bearing a propargyl acetate, giving 4-methoxy-5-alkylidenecyclopent-2-en-1-ones 4 via a degradation of the acetate group at the allyl cation intermediate. Beilstein-Institut 2013-08-27 /pmc/articles/PMC3778408/ /pubmed/24062838 http://dx.doi.org/10.3762/bjoc.9.202 Text en Copyright © 2013, Vasu et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms) |
spellingShingle | Full Research Paper Vasu, Dhananjayan Pawar, Samir Kundlik Liu, Rai-Shung Gold-catalyzed cyclization of allenyl acetal derivatives |
title | Gold-catalyzed cyclization of allenyl acetal derivatives |
title_full | Gold-catalyzed cyclization of allenyl acetal derivatives |
title_fullStr | Gold-catalyzed cyclization of allenyl acetal derivatives |
title_full_unstemmed | Gold-catalyzed cyclization of allenyl acetal derivatives |
title_short | Gold-catalyzed cyclization of allenyl acetal derivatives |
title_sort | gold-catalyzed cyclization of allenyl acetal derivatives |
topic | Full Research Paper |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3778408/ https://www.ncbi.nlm.nih.gov/pubmed/24062838 http://dx.doi.org/10.3762/bjoc.9.202 |
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