Insights into Synergistic Effects of Counterion and Ligand on Diastereoselectivity Switch in Gold-Catalyzed Post-Ugi Ipso-Cyclization

Overview

Journal ACS Omega

Publisher American Chemical Society

Specialty Chemistry

Date 2023 Jul 3

PMID 37396265

Authors

Jun He

Jie Zhang

Yunhe Li

Yan-Bo Han

Mengyang Li

Xiang Zhao

Affiliations

Soon will be listed here.

Abstract

The concept of diastereoselectivity switch in gold catalysis is investigated, which primarily depends on the effects of ligand and counterion. The origins of gold-catalyzed post-Ugi ipso-cyclization for the diastereoselective synthesis of spirocyclic pyrrol-2-one-dienone have been explored with density functional theory calculations. The reported mechanism emphasized the importance of the cooperation of ligand and counterion in diastereoselectivity switch, leading to the stereocontrolling transition states. Furthermore, the nonbonding interactions primarily between the catalyst and the substrate play a significant role in the cooperation of ligand and counterion. This work would be useful to further understand the reaction mechanism of gold-catalyzed cyclization and the effects of ligand and counterion.

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