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Simultaneous Control of Central and Helical Chiralities: Expedient Helicoselective Synthesis of Dioxa[6]helicenes

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.
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https://hal.archives-ouvertes.fr/hal-02953766
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Submitted on : Wednesday, September 30, 2020 - 1:40:21 PM
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Long-term archiving on: : Monday, January 4, 2021 - 8:46:12 AM

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Peng Liu, Xiaoze Bao, Jean-Valère Naubron, Sara Chentouf, Stéphane Humbel, et al.. Simultaneous Control of Central and Helical Chiralities: Expedient Helicoselective Synthesis of Dioxa[6]helicenes. Journal of the American Chemical Society, American Chemical Society, 2020, 142 (38), pp.16199-16204. ⟨10.1021/jacs.0c07995⟩. ⟨hal-02953766⟩

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