The atropo-enantioselective ring opening of achiral lactone-bridged biaryls using chirally modified aluminum hydrides

Article abstract of DOI:10.1055/s-1992-26126

The atropo-enantioselective preparation of the chiral biaryl 2-hydroxymethyl-1-(2-hydroxy-4,6-dimethoxyphenyl)naphthalene (7) from 1,3-dimethoxy-6H-benzo[b]naphtho[1,2-d]pyran-6-one (3) is described, whereby two formal problems of stereoselective biaryl synthesis are independently solved: The carbon-carbon bond formation by the intramolecular aryl coupling of the ester-type prefixed aromatic halves, and the asymmetric induction at the pre-formed biaryl axis by the subsequent stereoselective ring-opening reaction, using chiral hydrogen nucleophiles.