Simultaneous Control of Central and Helical Chiralities: Expedient Helicoselective Synthesis of Dioxa[6]helicenes
2020
Liu, Peng | Bao, Xiaoze | Naubron, Jean-Valère | Chentouf, Sara | Humbel, Stéphane | Vanthuyne, Nicolas | Jean, Marion | Giordano, Laurent | Rodriguez, Jean | Bonne, Damien
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.
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