Enantioselective Syntheses of Furan Atropisomers by an Oxidative Central-to-Axial Chirality Conversion Strategy

Vivek S Raut (1) , Marion Jean (1) , Nicolas Vanthuyne (1) , Christian Roussel (1) , Thierry Constantieux (1) , Cyril Bressy (1) , Xavier Bugaut (1) , Damien Bonne (1) , Jean Rodriguez (1)

1 ISM2 - Institut des Sciences Moléculaires de Marseille

For the first time, enantiomerically enriched atropoisomeric furans have been accessed using a central- to-axial chirality conversion strategy. Hence, oxidation of the enantioenriched dihydrofuran precursors gave rise to axially chiral furans with high enantiopurities accounting from excellent conversion percentages (cp) in most cases.

Mots clés: Furan atropisomers; conversion of chirality; organocatalysis; axial chirality

Domaines: Chimie organique

Vivek S Raut, Marion Jean, Nicolas Vanthuyne, Christian Roussel, Thierry Constantieux, et al.. Enantioselective Syntheses of Furan Atropisomers by an Oxidative Central-to-Axial Chirality Conversion Strategy. Journal of the American Chemical Society, 2017, 139 (6), pp.2140-2143. ⟨10.1021/jacs.6b11079⟩. ⟨hal-01533761⟩