Work

Decarboxylation-Driven Double Annulations: Innovative Multi-Component Reaction Pathways

Year: 2025

Type: article

Abstract: A concerted five-component reaction strategy has been developed, featuring double [3+2] cycloadditions utilizing aspartic acid. This approach provides valuable insights into mechanistic pathways, allowing for the distinction between concerted and stepwise processes based on reaction efficiency and diastereoselectivity. Both aspartic and glutamic acids have been employed for a thorough evaluation and exploration of decarboxylation-driven double annulations. This method effectively constructs pyrrolizidine frameworks through a concerted double 1,3-dipolar cycloaddition with aspartic acid, as well as tetrahydropyrrolizinones via three-component double annulations, which include decarboxylative 1,3-dipolar cycloaddition and lactamization with glutamic acid. These highly convergent, decarboxylation-driven multicomponent reactions (MCRs) efficiently produce fused polyheterocyclic systems while being environmentally friendly, generating only CO2 and water as byproducts.

Source: Molecules

DOI: 10.3390/molecules30071594

Authors: Desheng Zhan, Gang Yang, Tieli Zhou, Sashirekha Nallapati, Xiaofeng Zhang

Institutions: Changchun Normal University, Changchun University, Northeastern University, Harvard University, Dana-Farber Cancer Institute

Language: English

Topic: Multicomponent Synthesis of Heterocycles

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $3,258

OpenAlex ID: W4409104807

FWCI: 0.298

Cites: 39

Cited by: 1

Related to: 10