One-Pot, Telescoped Alkenylation of Amides via Stable Tetrahedral Intermediates as Lithium Enolate Precursors

[Image: see text] A mild and efficient telescoped procedure for the stereoselective alkenylation of simple, non-activated amides using LiCH(2)SiMe(3) and carbonyl compounds as surrogates of alkenyllithium reagents is reported. Our methodology relies on the formation of stable tetrahedral intermediat...

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Autores principales: Ghinato, Simone, Meazzo, Carolina, De Nardi, Federica, Maranzana, Andrea, Blangetti, Marco, Prandi, Cristina
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10243110/
https://www.ncbi.nlm.nih.gov/pubmed/37218660
http://dx.doi.org/10.1021/acs.orglett.3c01269
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author Ghinato, Simone
Meazzo, Carolina
De Nardi, Federica
Maranzana, Andrea
Blangetti, Marco
Prandi, Cristina
author_facet Ghinato, Simone
Meazzo, Carolina
De Nardi, Federica
Maranzana, Andrea
Blangetti, Marco
Prandi, Cristina
author_sort Ghinato, Simone
collection PubMed
description [Image: see text] A mild and efficient telescoped procedure for the stereoselective alkenylation of simple, non-activated amides using LiCH(2)SiMe(3) and carbonyl compounds as surrogates of alkenyllithium reagents is reported. Our methodology relies on the formation of stable tetrahedral intermediates, which, upon collapse into highly reactive lithium enolates in a solvent-dependent fashion, allows for the assembly of α,β-unsaturated ketones in a single synthetic operation with high stereoselectivity.
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spelling pubmed-102431102023-06-07 One-Pot, Telescoped Alkenylation of Amides via Stable Tetrahedral Intermediates as Lithium Enolate Precursors Ghinato, Simone Meazzo, Carolina De Nardi, Federica Maranzana, Andrea Blangetti, Marco Prandi, Cristina Org Lett [Image: see text] A mild and efficient telescoped procedure for the stereoselective alkenylation of simple, non-activated amides using LiCH(2)SiMe(3) and carbonyl compounds as surrogates of alkenyllithium reagents is reported. Our methodology relies on the formation of stable tetrahedral intermediates, which, upon collapse into highly reactive lithium enolates in a solvent-dependent fashion, allows for the assembly of α,β-unsaturated ketones in a single synthetic operation with high stereoselectivity. American Chemical Society 2023-05-23 /pmc/articles/PMC10243110/ /pubmed/37218660 http://dx.doi.org/10.1021/acs.orglett.3c01269 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Ghinato, Simone
Meazzo, Carolina
De Nardi, Federica
Maranzana, Andrea
Blangetti, Marco
Prandi, Cristina
One-Pot, Telescoped Alkenylation of Amides via Stable Tetrahedral Intermediates as Lithium Enolate Precursors
title One-Pot, Telescoped Alkenylation of Amides via Stable Tetrahedral Intermediates as Lithium Enolate Precursors
title_full One-Pot, Telescoped Alkenylation of Amides via Stable Tetrahedral Intermediates as Lithium Enolate Precursors
title_fullStr One-Pot, Telescoped Alkenylation of Amides via Stable Tetrahedral Intermediates as Lithium Enolate Precursors
title_full_unstemmed One-Pot, Telescoped Alkenylation of Amides via Stable Tetrahedral Intermediates as Lithium Enolate Precursors
title_short One-Pot, Telescoped Alkenylation of Amides via Stable Tetrahedral Intermediates as Lithium Enolate Precursors
title_sort one-pot, telescoped alkenylation of amides via stable tetrahedral intermediates as lithium enolate precursors
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10243110/
https://www.ncbi.nlm.nih.gov/pubmed/37218660
http://dx.doi.org/10.1021/acs.orglett.3c01269
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