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One-Pot, Telescoped Alkenylation of Amides via Stable Tetrahedral Intermediates as Lithium Enolate Precursors.
- Source :
-
Organic letters [Org Lett] 2023 Jun 02; Vol. 25 (21), pp. 3904-3909. Date of Electronic Publication: 2023 May 23. - Publication Year :
- 2023
-
Abstract
- A mild and efficient telescoped procedure for the stereoselective alkenylation of simple, non-activated amides using LiCH <subscript>2</subscript> SiMe <subscript>3</subscript> 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.
Details
- Language :
- English
- ISSN :
- 1523-7052
- Volume :
- 25
- Issue :
- 21
- Database :
- MEDLINE
- Journal :
- Organic letters
- Publication Type :
- Academic Journal
- Accession number :
- 37218660
- Full Text :
- https://doi.org/10.1021/acs.orglett.3c01269