An efficient and practical entry to 2-amido-dienes and 3-amido-trienes from allenamides through stereoselective 1,3-hydrogen shifts

Preparations of de novo acyclic 2-amido-dienes and 3-amido-trienes through 1,3-hydrogen shifts from allenamides are described. These 1,3-hydrogen shifts could be achieved thermally or they could be promoted by the use of Brønsted acids. Under either condition, these processes are highly regioselecti...

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Autores principales: Hayashi, Ryuji, Feltenberger, John B, Lohse, Andrew G, Walton, Mary C, Hsung, Richard P
Formato: Texto
Lenguaje:English
Publicado: Beilstein-Institut 2011
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3079123/
https://www.ncbi.nlm.nih.gov/pubmed/21512601
http://dx.doi.org/10.3762/bjoc.7.53
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author Hayashi, Ryuji
Feltenberger, John B
Lohse, Andrew G
Walton, Mary C
Hsung, Richard P
author_facet Hayashi, Ryuji
Feltenberger, John B
Lohse, Andrew G
Walton, Mary C
Hsung, Richard P
author_sort Hayashi, Ryuji
collection PubMed
description Preparations of de novo acyclic 2-amido-dienes and 3-amido-trienes through 1,3-hydrogen shifts from allenamides are described. These 1,3-hydrogen shifts could be achieved thermally or they could be promoted by the use of Brønsted acids. Under either condition, these processes are highly regioselective in favour of the α-position, and highly stereoselective in favour of the E-configuration. In addition, 6π-electron electrocyclic ring-closure could be carried out with 3-amido-trienes to afford cyclic 2-amido-dienes, and such electrocyclic ring-closure could be rendered in tandem with the 1,3-hydrogen shift.
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spelling pubmed-30791232011-04-21 An efficient and practical entry to 2-amido-dienes and 3-amido-trienes from allenamides through stereoselective 1,3-hydrogen shifts Hayashi, Ryuji Feltenberger, John B Lohse, Andrew G Walton, Mary C Hsung, Richard P Beilstein J Org Chem Full Research Paper Preparations of de novo acyclic 2-amido-dienes and 3-amido-trienes through 1,3-hydrogen shifts from allenamides are described. These 1,3-hydrogen shifts could be achieved thermally or they could be promoted by the use of Brønsted acids. Under either condition, these processes are highly regioselective in favour of the α-position, and highly stereoselective in favour of the E-configuration. In addition, 6π-electron electrocyclic ring-closure could be carried out with 3-amido-trienes to afford cyclic 2-amido-dienes, and such electrocyclic ring-closure could be rendered in tandem with the 1,3-hydrogen shift. Beilstein-Institut 2011-04-07 /pmc/articles/PMC3079123/ /pubmed/21512601 http://dx.doi.org/10.3762/bjoc.7.53 Text en Copyright © 2011, Hayashi 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
Hayashi, Ryuji
Feltenberger, John B
Lohse, Andrew G
Walton, Mary C
Hsung, Richard P
An efficient and practical entry to 2-amido-dienes and 3-amido-trienes from allenamides through stereoselective 1,3-hydrogen shifts
title An efficient and practical entry to 2-amido-dienes and 3-amido-trienes from allenamides through stereoselective 1,3-hydrogen shifts
title_full An efficient and practical entry to 2-amido-dienes and 3-amido-trienes from allenamides through stereoselective 1,3-hydrogen shifts
title_fullStr An efficient and practical entry to 2-amido-dienes and 3-amido-trienes from allenamides through stereoselective 1,3-hydrogen shifts
title_full_unstemmed An efficient and practical entry to 2-amido-dienes and 3-amido-trienes from allenamides through stereoselective 1,3-hydrogen shifts
title_short An efficient and practical entry to 2-amido-dienes and 3-amido-trienes from allenamides through stereoselective 1,3-hydrogen shifts
title_sort efficient and practical entry to 2-amido-dienes and 3-amido-trienes from allenamides through stereoselective 1,3-hydrogen shifts
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3079123/
https://www.ncbi.nlm.nih.gov/pubmed/21512601
http://dx.doi.org/10.3762/bjoc.7.53
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