Asymmetric synthesis of highly substituted spiro[2H-pyrrole-2,3-succinimide] derivatives by copper-catalyzed post-Ugi reactions

Abstract

Herein we present a novel one-por methodology for the synthesis of enantioenriched 2H-pyrrolespirosuccinimides by copper-catalyzed reactions on Ugi adducts derived from enantiopure α-alkylbenzyl amines through a chirality transfer process. We have proposed a mechanism supported by density functional theory (DFT) calculations, where a hydrogen radical-shuttle (HRS) process explains the chemical and stereochemical results. This work demonstrates the efficient stereoselective synthesis of structurally unique, highly functionalized nitrogen heterocyclic systems using simple protocols and affordable starting materials.