Impact Factor:8.1
DOI number:10.1039/D5SC10040B
Journal:Chem. Sci
Abstract:The catalytic asymmetric synthesis of inherently chiral calix[4]arenes, a distinct class of chiral macrocycles with significant applications in asymmetric catalysis, chiral recognition and functional materials, remains a formidable challenge. Moreover, strategies for the simultaneous introduction of multiple stereogenic elements within these scaffolds in a single transformation are highly desirable yet underdeveloped. Herein, we report a one-step protocol that concurrently installs both C–C axial and inherent chirality in a calix[4]arene system through palladium/chiral norbornene (Pd/NBE*) cooperative catalysis. This approach provides direct access to a diverse array of five- and six-membered benzo-fused calix[4]arenes (30 examples) with consistently high enantioselectivity and diastereoselectivity. Notably, the obtained products can be readily transformed into monophosphine ligands bearing both C–C axial and inherent chirality, which exhibit excellent stereocontrol in a silver-catalysed asymmetric [3 + 2] cyclization reaction. Preliminary photophysical and chiroptical studies reveal that these dual-chiral calix[4]arenes exhibit promising glum factors, demonstrating their potential as versatile chiral scaffolds for advanced organic optoelectronic materials.
Indexed by:Journal paper
Discipline:Natural Science
Volume:17
Issue:18
Page Number:8968-8975
ISSN No.:2041-6520
Translation or Not:no
Date of Publication:2026-03-04
Included Journals:SCI
Links to published journals:https://pubs.rsc.org/en/content/articlelanding/2026/sc/d5sc10040b
Date of Publication:2026-03-04