Gold(i)-catalyzed [2 + 2 + 2] cycloaddition of allenamides, alkenes and aldehydes: a straightforward approach to tetrahydropyrans

Allenamides participate as two-carbon components in an intermolecular [2 + 2 + 2] cycloaddition with alkenes and aldehydes when treated with catalytic amounts of a phosphite gold complex. The reaction is highly regio- and chemoselective, and works with different types of alkenes, including styrenes,...

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Autores principales: Faustino, Hélio, Varela, Iván, Mascareñas, José L., López, Fernando
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2015
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5655898/
https://www.ncbi.nlm.nih.gov/pubmed/29308168
http://dx.doi.org/10.1039/c5sc00295h
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author Faustino, Hélio
Varela, Iván
Mascareñas, José L.
López, Fernando
author_facet Faustino, Hélio
Varela, Iván
Mascareñas, José L.
López, Fernando
author_sort Faustino, Hélio
collection PubMed
description Allenamides participate as two-carbon components in an intermolecular [2 + 2 + 2] cycloaddition with alkenes and aldehydes when treated with catalytic amounts of a phosphite gold complex. The reaction is highly regio- and chemoselective, and works with different types of alkenes, including styrenes, enol ethers or enamides, as well as with aromatic and aliphatic aldehydes. Accordingly, different types of 2,6-disubstituted tetrahydropyrans can be stereoselectively assembled in a single step from commercial or very accessible starting materials.
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spelling pubmed-56558982018-01-05 Gold(i)-catalyzed [2 + 2 + 2] cycloaddition of allenamides, alkenes and aldehydes: a straightforward approach to tetrahydropyrans Faustino, Hélio Varela, Iván Mascareñas, José L. López, Fernando Chem Sci Chemistry Allenamides participate as two-carbon components in an intermolecular [2 + 2 + 2] cycloaddition with alkenes and aldehydes when treated with catalytic amounts of a phosphite gold complex. The reaction is highly regio- and chemoselective, and works with different types of alkenes, including styrenes, enol ethers or enamides, as well as with aromatic and aliphatic aldehydes. Accordingly, different types of 2,6-disubstituted tetrahydropyrans can be stereoselectively assembled in a single step from commercial or very accessible starting materials. Royal Society of Chemistry 2015-05-01 2015-03-02 /pmc/articles/PMC5655898/ /pubmed/29308168 http://dx.doi.org/10.1039/c5sc00295h Text en This journal is © The Royal Society of Chemistry 2015 http://creativecommons.org/licenses/by/3.0/ This is an Open Access article distributed under the terms of the Creative Commons Attribution 3.0 Unported License (http://creativecommons.org/licenses/by/3.0/) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Chemistry
Faustino, Hélio
Varela, Iván
Mascareñas, José L.
López, Fernando
Gold(i)-catalyzed [2 + 2 + 2] cycloaddition of allenamides, alkenes and aldehydes: a straightforward approach to tetrahydropyrans
title Gold(i)-catalyzed [2 + 2 + 2] cycloaddition of allenamides, alkenes and aldehydes: a straightforward approach to tetrahydropyrans
title_full Gold(i)-catalyzed [2 + 2 + 2] cycloaddition of allenamides, alkenes and aldehydes: a straightforward approach to tetrahydropyrans
title_fullStr Gold(i)-catalyzed [2 + 2 + 2] cycloaddition of allenamides, alkenes and aldehydes: a straightforward approach to tetrahydropyrans
title_full_unstemmed Gold(i)-catalyzed [2 + 2 + 2] cycloaddition of allenamides, alkenes and aldehydes: a straightforward approach to tetrahydropyrans
title_short Gold(i)-catalyzed [2 + 2 + 2] cycloaddition of allenamides, alkenes and aldehydes: a straightforward approach to tetrahydropyrans
title_sort gold(i)-catalyzed [2 + 2 + 2] cycloaddition of allenamides, alkenes and aldehydes: a straightforward approach to tetrahydropyrans
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5655898/
https://www.ncbi.nlm.nih.gov/pubmed/29308168
http://dx.doi.org/10.1039/c5sc00295h
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