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

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 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.

Language: Английский

Base-Promoted Cascade Vinylogous Michael/Michael Addition of Alkylidene Succinimides for the Construction of Penta-Substituted Cyclopentanes

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

A base-catalyzed cascade vinylogous Michael/Michael addition of alkylidene succinimides and oxindole-derived pyrazolones has been developed for the construction penta-substituted cyclopentanes.

Language: Английский