Highly stereospecific conversion of C-centrochirality of a 3,4-dihydro-2H-1,1′-binaphthalen-1-ol into axial chirality of a 3,4-dihydro-1,1′-binaphthalene

C-Centrochirality of 3,4-dihydro-2′-methoxy-2-methyl-2H-1,1′-binaphthalen-1-ol (R,R)-3e, which had been prepared by diastereoselective 1,2-addition of a 2-methoxy-1-naphthylytterbium reagent to 2-methyl-1-tetralone (R)-1b, was stereospecifically converted into axial chirality of 3,4-dihydro-2′-methoxy-2-methyl-1,1′-binaphthalene (aR)-4 with up to 95% ee by dehydration with trifluoroacetic anhydride. DDQ aromatization of (aR)-4 gave 2′-methoxy-2-methyl-1,1′-binaphthalene (aR)-5 without appreciable loss of the axial integrity. The net process provides a potential access to nonracemic 1,1′-binaphthalenes.