Work

Merging Enantioselective Lewis Base Organocatalysis and Gold(I) Catalysis: A One-Pot Access to Chiral-Fused Polycyclic Compounds

Year: 2025

Type: article

Abstract: Reported herein is a route to functionalized chiral heteroaromatic polycyclic compounds leveraging two unfriendly catalytic cycles in a one-pot sequential process. α-Heteroaromatic-γ-butyrolactones were engaged in a highly regio-, diastereo-, and enantio-selective Lewis base asymmetric allylic alkylation (AAA) with alkyne-functionalized Morita-Baylis-Hillman (MBH) carbonates. Gratefully, due to the low Lewis base catalyst loading, subsequent gold-catalyzed Friedel-Crafts type cyclization, entailing the formation of fused polycyclic compounds, proceeded efficiently, affording structurally complex, highly enantioenriched products.

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.5c00051

Authors: Rémi Pereira, Pierre Locquet, Aurélien Blanc, Fabienne Grellepois, Emmanuel Riguet

Institutions: Centre National de la Recherche Scientifique, Institut de Chimie Moléculaire de Reims, Université de Reims Champagne-Ardenne, Institut de Chimie de Strasbourg, Université de Strasbourg

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green