Synthesis of Trisubstituted Alkenes Bearing a Quaternary Carbon by Lewis-Acid Catalyzed Regioselective Reaction of Internal Alkynols with 2-Pyrrolylanilines

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

Published: March 24, 2025

Substituted alkenes, crucial in organic chemistry, are typically accessed from internal alkynes by using transition-metal catalysis. Herein, we report a novel approach to the Lewis acid-catalyzed synthesis of trisubstituted alkenes bearing quaternary carbon alkynols and 2-pyrrolyl arylamines. This method involves allene formation followed intramolecular [5 + 1] annulation furnish diverse range with excellent regioselectivity poor diastereoselectivity. Further, demonstrated gram-scale synthetic transformations proposed reaction mechanism based on isolation intermediates.

Language: Английский

Ag(I)-Catalyzed Tandem Cyclization–Cycloaddition–Isomerization Reaction of 2-Alkynylbenzaldoxime with Bicyclobutane: A Route to Multiply Substituted Cyclobutanols

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: April 1, 2025

Multiply substituted cyclobutanols are pivotal synthetic intermediates for constructing complex molecular architectures via ring-opening strategies. The development of efficient methods these valuable building blocks has garnered significant interest in the chemical community. In this work, we have described a novel silver(I)-catalyzed tandem cyclization–cycloaddition–isomerization sequence with bicyclobutanes and 2-alkynylbenzaldoximes, which offered an effective route to multiply cyclobutanols. This protocol features mild conditions, remarkable stereospecificity, broad substrate scope, excellent functional group tolerance. addition, application potential reaction was readily proven by its high efficiency reactants bearing biological moieties scale-up experiments.

Language: Английский