Advances in the Synthesis of Cyclopropylamines

Chemical Reviews, Journal Year: 2025, Volume and Issue: unknown

Published: March 6, 2025

Cyclopropylamines are an important subclass of substituted cyclopropanes that combine the unique electronic and steric properties with presence a donor nitrogen atom. In addition to their in diverse array biologically active compounds, cyclopropylamines utilized as synthetic intermediates, particularly ring-opening or cycloaddition reactions. Consequently, synthesis these compounds has constituted significant research topic, evidenced by abundant published methods. widely used Curtius rearrangement, classical cyclopropanation methods have been adapted integrate function (Simmons-Smith reaction, metal-catalyzed reaction diazo on olefins, Michael-initiated ring-closure reactions) advances enantioselective synthesis. More recently, specific developed for preparation aminocyclopropane moiety (Kulinkovich reactions applied amides nitriles, cyclopropenes, involving C-H functionalization, ...). The topic this review is present different cyclopropylamine derivatives, aim covering methodological best possible, highlighting scope, stereochemical aspects future trends.

Language: Английский

Copper‐Catalyzed Dearomative Cyclization of Indolyl Ynamides for Synthesis of Pentacyclic Spiroindolines

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 23, 2024

Abstract The dearomatization of indoles with ynamides is a convenient access towards polycyclic spiroindolines, which can be initiated by α‐ and β‐additions ynamides. Currently, the related β‐addition dearomative cyclization requires noble‐metal catalyst or stoichiometric oxidant. Herein, we report copper‐catalyzed aryl‐substituted indolyl through regioselective onto ynamides, providing pentacyclic spiroindolines in 81–97% yields >25:1 diastereoselectivities. Moreover, preliminary success has been obtained for catalytic enantioselective cyclization.

Language: Английский