NHC-Catalyzed Allylation of Aldehydes with MBH Carbonates and Their Michael Addition–Elimination-Cope Rearrangement Cascade: A Route to rac-Sacubitril DOI

Tushar B. Kale,

Sayali G. Jagtap,

Santosh B. Mhaske

и другие.

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

A Formal [4+1] Annulation incorporating Styrylogous Aldol Condensation to Access Substituted 2-Styryl-benzofurans DOI

Manyam Subbi Reddy,

K. Kamala,

Surisetti Suresh

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

A styrylogous aldol condensation has been introduced, constructing 2-styryl-benzofurans in high yields. The method's application demonstrated the efficient syntheses of biologically active aminostyryl-benzofurans good overall

Язык: Английский

Процитировано

0
NHC-Catalyzed Allylation of Aldehydes with MBH Carbonates and Their Michael Addition–Elimination-Cope Rearrangement Cascade: A Route to rac-Sacubitril DOI

Tushar B. Kale,

Sayali G. Jagtap,

Santosh B. Mhaske

и другие.

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

Процитировано

0