Palladium catalyzed stereoselective intramolecular [3 + 2] cycloaddition reactions of () & ()-ene-vinylidenecyclopropanes.

Org Biomol Chem

Key Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry & Molecular Engineering, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, China.

Published: June 2024

AI Article Synopsis

  • - A new reaction method using palladium that opens and closes rings has been developed for specific types of compounds, known as vinylidenecyclopropanes, to create complex bicyclic structures.
  • - The process involves an intramolecular cycloaddition that relies on a bulky biaryl phosphine ligand, leading to the formation of fused bicyclic products with strong control over the stereochemistry.
  • - The study suggests a reasonable mechanism for this reaction, supported by earlier research and advanced computational methods, indicating a wider applicability and tolerance for various functional groups in the substrate.

Article Abstract

A palladium-catalyzed ring-opening cyclization of () & ()-ene-vinylidenecyclopropanes has been developed an intramolecular [3 + 2] cycloaddition process in the presence of a sterically bulky biaryl phosphine ligand, stereoselectively affording fused - & -bicyclo[4.3.0] skeletal products in good yields with a broad substrate scope and good functional tolerance. A plausible reaction mechanism was proposed on the basis of previous work and the DFT calculations.

Download full-text PDF

Source
http://dx.doi.org/10.1039/d4ob00607kDOI Listing

Publication Analysis

Top Keywords

intramolecular cycloaddition
8
palladium catalyzed
4
catalyzed stereoselective
4
stereoselective intramolecular
4
cycloaddition reactions
4
reactions -ene-vinylidenecyclopropanes
4
-ene-vinylidenecyclopropanes palladium-catalyzed
4
palladium-catalyzed ring-opening
4
ring-opening cyclization
4
cyclization -ene-vinylidenecyclopropanes
4

Similar Publications

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!