Neighboring Lithium-Assisted [1,2]-Wittig Rearrangement: Practical Access to Diarylmethanol-Based 1,4-Diols and Optically Active BINOL Derivatives with Axial and sp3-Central Chirality

A facile and practical methodology for the synthesis of synthetically useful diarylmethanol-based 1,4-diols and enantiomerically pure BINOL-derived diols with axial and sp(3)-central chirality has been developed through neighboring lithium-promoted [1,2]-Wittig rearrangement. The chirality transfer process shows a broad substrate scope in terms of the aromatic ether substituent, which allows access to a broad of range of chiral 1,1'-binaphthalene-2-alpha-arylmethanol-2'-ols with excellent enantioselectivities (> 99% enantiomeric excess) and yields (84-96%). This should be considered as an available and attractive chiral source to design and prepare privileged ligands or catalysts.