Diastereoselective synthesis of indolenine-based spiro[pyrazolone-4,2′-pyrrolidine] scaffolds via 1,3-dipolar cycloaddition of 4-aminopyrazolones, aldehydes, and indolenines

Abstract

In this work, we report a one-pot [3 + 2] cycloaddition of 4-aminopyrazolones, indolenines, and aldehydes. The reaction utilized in situ generated azomethine ylides as 1,3-dipoles and 2-alkenylindolenines as dipolarophiles affording indolenine-derived spiro[pyrazolone-4,2′-pyrrolidine] scaffolds with four contiguous stereocenters with excellent yields (up to 95%) and diastereoselectivities (up to >20 : 1 dr) under simple conditions. The in situ generation of azomethine ylides and dipolarophiles in one pot is a unique feature of this process.