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

Peng Liu (1) , Xiaoze Bao (2) , Jean-Valère Naubron (3) , Sara Chentouf (3) , Stéphane Humbel (1) , Nicolas Vanthuyne (1) , Marion Jean (1) , Laurent Giordano (1) , Jean Rodriguez (1) , Damien Bonne (1)

1 ISM2 - Institut des Sciences Moléculaires de Marseille
2 college of pharmaceutical science & collaborative innovation center of Yangtze River Delta Region Green Pharmaceuticals
3 FSCM - Fédération des Sciences Chimiques de Marseille

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.

Mots clés: heterohelicenes; multiple stereogenic elements; enantioselective organocatalysis

Domaines: Chimie organique

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, 2020, 142 (38), pp.16199-16204. ⟨10.1021/jacs.0c07995⟩. ⟨hal-02953766⟩