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

ABSTRACT: A mild and efficient telescoped procedure for the stereoselective alkenylation of simple, non-activated amides using LiCH₂SiMe₃ 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.

SUBMITTER: Ghinato S

PROVIDER: S-EPMC10243110 | biostudies-literature | 2023 Jun

REPOSITORIES: biostudies-literature

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

Ghinato Simone S Meazzo Carolina C De Nardi Federica F Maranzana Andrea A Blangetti Marco M Prandi Cristina C

Organic letters 20230523 21

A mild and efficient telescoped procedure for the stereoselective alkenylation of simple, non-activated amides using LiCH<sub>2</sub>SiMe<sub>3</sub> 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 stereoselect ...[more]

PMID: 37218660

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