Tertiary Amine‐Catalyzed Stereoretentive Multi‐Component Cascade Reaction of Carboxylic Acids: Facile Synthesis of Cyclic Ureas/Urethanes DOI
Yi Hu,

Yifei Cai,

Yanfei Liu

и другие.

Chinese Journal of Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Май 29, 2025

Comprehensive Summary Herein, we developed a tertiary amine‐catalyzed stereoretentive multi‐component cascade reaction featuring an amidation/[4 + 1] annulation/decarboxylation/Curtius rearrangement/[2 n ] annulation sequence. This metal‐free and step‐economic method provided broad range of cyclic ureas/urethanes in green solvent under mild conditions without employing explosive toxic reagents. Importantly, this generated isocyanates situ catalytic via decarboxylation/Curtius rearrangement process dioxazolones.

Язык: Английский

Stereoselective Synthesis of Atropisomeric Amides Enabled by Intramolecular Acyl Transfer DOI Creative Commons
Jack M. Wootton,

Natalie J. Roper,

C. Morris

и другие.

Chemical Science, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

A stereoselective strategy to make C–N atropisomeric amides based on intramolecular acyl transfer via a tethered Lewis basic pyridine or tertiary amine group is reported.

Язык: Английский

Процитировано

0

Nucleophile-Controlled Regiodivergent Domino Reactions of Enetriones with γ-Bromocrotonates: Access to 1,3-Dienic Esters and Tetrasubstituted Pyrans DOI

Dan Xiong,

Sen Zhang, Zhiyue Li

и другие.

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Апрель 23, 2025

Herein, we developed an efficient nucleophile-controlled regiodivergent domino reaction between enetriones and γ-bromocrotonates. This method allowed for the rapid synthesis of a range 1,3-dienic esters tetrasubstituted pyrans under metal-free conditions. In presence pyridine, SN2 substitution/Michael addition/elimination sequence formed in satisfactory yields with high E-stereoselectivities. Alternatively, addition/cyclization/cyclopropanation/cyclopropane ring-opening process forged good help Et3N. It is interesting to note that site-selective reactions γ-bromocrotonates at α- or γ-position were readily realized by modulating pyridine Furthermore, simple Et3N act as both nucleophiles substitution Lewis bases deprotonation processes.

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

Tertiary Amine‐Catalyzed Stereoretentive Multi‐Component Cascade Reaction of Carboxylic Acids: Facile Synthesis of Cyclic Ureas/Urethanes DOI
Yi Hu,

Yifei Cai,

Yanfei Liu

и другие.

Chinese Journal of Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Май 29, 2025

Comprehensive Summary Herein, we developed a tertiary amine‐catalyzed stereoretentive multi‐component cascade reaction featuring an amidation/[4 + 1] annulation/decarboxylation/Curtius rearrangement/[2 n ] annulation sequence. This metal‐free and step‐economic method provided broad range of cyclic ureas/urethanes in green solvent under mild conditions without employing explosive toxic reagents. Importantly, this generated isocyanates situ catalytic via decarboxylation/Curtius rearrangement process dioxazolones.

Язык: Английский

Процитировано

0