Enhanced Reactivity for the Wagner-Jauregg Reaction Under Aqueous Conditions.

ABSTRACT: The Wagner-Jauregg reaction produces up to four new carbon-carbon bonds and eight new stereocenters, but limitations, such as high requisite temperatures, a restricted substrate scope, and significant undesired polymer formation, have resulted in this reaction receiving minimal attention. While generally considered a subtype of the Diels-Alder reaction, in which a styrenyl diene is employed in a tandem double-Diels-Alder reaction, a second, structurally distinct, stereochemically complex product can also be produced by the Wagner-Jauregg reaction, resulting from a Diels-Alder-ene cascade. Very few attempts to improve reaction conditions, expand substrate scope, or optimize product selectivity have been published. Through reaction optimization, supplemented by density functional theory calc

SUBMITTER: Barton K 

PROVIDER: S-EPMC12809351 | biostudies-literature | 2026 Jan

REPOSITORIES: biostudies-literature