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 o f a 2-methoxy-1-naphthylytterbium reagent to 2-methyl-1-tetralone (R)-1b, w as stereospecifically converted into axial chirality of 3,4-dihydro-2'-meth oxy-2-methyl-1,1'-binaphthalene (aR)-4 with up to 95% ee by dehydration wit h trifluoroacetic anhydride. DDQ aromatization of (aR)-4 gave 2'-methoxy-2- methyl-1,1'-binaphthalene (aR)-5 without appreciable loss of the axial inte grity. The net process provides a potential access to nonracemic 1,1'-binap hthalenes. (C) 2001 Elsevier Science Ltd. All rights reserved.