A new and practical method for preparing enantiomerically pure [1,1′-binaphthalene]-2,2′-diol: Resolution of racemic [1,1′-binaphthalene]-2,2′-diol with threo-(1s,2s)-2-amino-1-(4-nitrophenyl)propane-1,3-diol-cyclohexanone condensate

Article abstract of DOI:10.1002/hlca.200390006

An economic and practical method for preparing enantiomerically pure [1,1′-binaphthalene]-2,2′-diols is reported. Thus, a condensate of threo-(1S,2S)-2-amino-1-(4-nitrophenyl)propane-1,3-diol and cyclohexanone (CHANP) was used as a resolving agent. A 2:1:1 mixture of racemic [1,1′-binaphthalene]-2,2′-diol, boric acid, and CHANP was refluxed for several hours in THF or MeCN to give a white precipitate of bis((R)-[1,1′-binaphthalene]-2,2′-diol}boric acid CHANP derivative, from the precipitate, and a filtrate separated from the precipitate, (R)- and (S)-[1,1′-binaphthalene]-2,2′-diol of 100% ee were obtained in ca. 65% yield, respectively.