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Updated: Sep 26, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Solvent-controlled divergent (4 + 1) cycloaddition of 1,4-enynoates with amines: modular synthesis of pyrroles
Jianghong Tan1, Lu Zhang1, Dale Wu1
1College of Chemistry, Zhengzhou University, Zhengzhou 450001, P. R. China. lierqing@zzu.edu.cn.
Abstract:
A metal-free, solvent-controlled chemodivergent (4 + 1) cycloaddition of hex-5-en-2-ynoates with primary amines for the modular assembly of tetrahydropyrroles and dihydropyrroles is reported. Simply switching between HFIP and DME enables selective access to two distinct pyrrolidine-type skeletons from identical starting materials under mild conditions. This transformation tolerates diverse functional groups and complex bio-relevant amine substrates, permitting late-stage skeleton diversification. Mechanistic studies reveal that solvent-modulated hydrogen-bonding interactions alter the cyclization pathway after aza-Michael addition, governing the observed chemoselectivity.
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