Work

Multistep Cascade Catalyzed by a Single-Chiral Lewis Acid: Efficient Asymmetric Synthesis of Macrocyclic Chiral Dilactones and Dilactams

Year: 2025

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide A Cu(II)-catalyzed asymmetric cascade process was successfully developed by the dimerization of β,γ-unsaturated α-keto tryptophol esters or β,γ-unsaturated α-keto tryptamino amides under mild reaction conditions, furnishing the corresponding macrocyclic dilactones and dilactams in good yields with excellent regio-, diastereo-, and enantioselectivities. The transformation involved a four-step cascade of double Friedel–Crafts alkylation and double N -hemiketalization, providing efficient access to a variety of macrocyclic dilactone and dilactam scaffolds bearing four new stereocenters in a one-pot and highly atom-economic fashion. The resultant chiral macrocyclic compounds were further applied as ligands in the copper-catalyzed asymmetric Friedel–Crafts alkylation reactions and also tested as multifunctional chiral host molecules in binding with quinine and quinidine.

Source: JACS Au

DOI: 10.1021/jacsau.5c00069

Authors: Bai-Lin Wang, Jie-Qiang Yu, Qian Zhang, Xing-Wang Wang

Institutions: Soochow University, Hangzhou Normal University

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $3,500

Funders: Royal Society of Chemistry, National Natural Science Foundation of China, Priority Academic Program Development of Jiangsu Higher Education Institutions, Program for New Century Excellent Talents in University