Simultaneous Control of Central and Helical Chiralities: Expedient Helicoselective Synthesis of Dioxa[6]helicenes
Peng Liu, Xiaoze Bao, Jean‐Valère Naubron, Sara Chentouf, Stéphane Humbel, Nicolas Vanthuyne, Marion Jean, Laurent Giordano, Jean Rodriguez, Damien Bonne
Abstract
An expedient synthesis of a new family of configurationally stable dioxa[6]helicenes was established using a sequential helicoselective organocatalyzed heteroannulation/eliminative aromatization via enantioenriched fused 2-nitro dihydrofurans featuring both central and helical chiralities. Starting from simple achiral precursors, a broad range of these previously unknown chiral heterocyclic scaffolds were obtained with good efficiency, and their aromatization proceeded with very high enantiopurity retention in most cases.
Topics & Concepts
ChemistryAromatizationCombinatorial chemistryStereochemistryOrganic chemistryCatalysisSynthesis and Properties of Aromatic CompoundsAxial and Atropisomeric Chirality SynthesisMolecular spectroscopy and chirality