Organic Letters, Год журнала: 2025, Номер unknown
Опубликована: Май 28, 2025
We report herein a novel NHC-catalyzed transition-metal-free chemoselective allylation of aldehydes with Morita-Baylis-Hillman (MBH) carbonates using an inorganic base. Fascinatingly, the use organic base follows different mechanism, leading to highly functionalized 1,5-dienes via Michael addition-elimination reaction followed by [3,3]-sigmatropic Cope rearrangement. The described method harnesses new Csp2-Csp3 bond access α-methylene-γ-oxo-γ-substituted ester derivatives paving way facile synthesis potent natural products and active pharmaceutical ingredients (APIs). A broad range aromatic aliphatic MBH was employed provide variety interesting butanoate dienyl ketone scaffolds in good excellent yields. This chemistry has been extended efficient syntheses rac-sacubitril API γ-butyrolactone scaffold, which is privileged core present many APIs.
Язык: Английский