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

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...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2020-09, Vol.142 (38), p.16199-16204
Main Authors: Liu, Peng, Bao, Xiaoze, Naubron, Jean-Valère, Chentouf, Sara, Humbel, Stéphane, Vanthuyne, Nicolas, Jean, Marion, Giordano, Laurent, Rodriguez, Jean, Bonne, Damien
Format: Article
Language:English
Subjects:
Chemical Sciences
Organic chemistry
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Summary: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.0c07995