Application of the Russig-Laatsch reaction to synthesize a bis[5]helicene chiral pocket for asymmetric catalysis

The enantiomers of a bis[5]helicenediol Ligand ([5]HELOL) have been synthesized in appreciable amounts by a procedure in which key steps are the union of p-benzoquinone with an enol ether of 3-acetylphenanthrene and the displacement of phenol and phenol ether functions by alcohols (the Russig-Laatsch reaction). This diol catalyzes the addition of diethylzinc to aldehydes and gives nonracemic alcohols with enantiomeric excesses as high as 81%. The stereoselectivities and yields are much greater than when the catalyzing diol is BINOL. The enantioselectivities are greater also than those of other reactions catalyzed by helicene ligands.