Stereocontrolled Construction of Spirooxindole-Containing 5,6,7,8-Tetrahydropyrrolo[1,2-a]pyridine via Michael/Friedel–Crafts Domino Reaction Promoted by Secondary Amine-Squaramide

Organic Letters, Journal Year: 2024, Volume and Issue: 26(11), P. 2152 - 2157

Published: March 8, 2024

An asymmetric Michael/Friedel–Crafts cascade reaction with Morita–Baylis–Hillman (MBH) nitroallylic esters and 3-pyrrolyloxindoles has been developed for the stereoselective construction of spirooxindole-containing tetrahydroindolizines. A range tetracyclic scaffolds possessing three consecutive chiral centers, including an all-carbon quaternary stereocenter, were generated in 53–85% isolated yields high diastereoselectivities enantiopurities (≥3:1 dr, 50–98% ee). newly synthesized bifunctional secondary amine/squaramide organocatalyst was demonstrated to exhibit better stereochemical control than their tertiary analogues.

Language: Английский

Synthesis of Aza‐Bicyclic Maleimide Skeleton by Addition‐Ring Opening Cascade Reaction of Vinylogous Oxindole

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(20)

Published: April 1, 2024

Abstract An efficient method has been developed to facilitate the addition‐ring opening cascade reaction of vinylogous oxindole, resulting in synthesis a variety aza‐bicyclic maleimide derivatives with high yields and exceptional diastereoselectivities. Furthermore, product could be effectively easily transformed into difluoromethylenecyclohexane skeleton through dehydrofluorination process. This methodology demonstrates significant potential for skeleton, which possesses biological or pharmaceutical activity.

Language: Английский