Synthesis of 3 or 3,3′-substituted BINOL ligands and their application in the asymmetric addition of diethylzinc to aromatic aldehydes

Three new substituted BINOL ligands (R)-3-[4,6-bis(dimethylamino)-1,3,5-triazin-2-yl]-1,1'-bi-2-naphthol (R)-1, (R)3,3'-bis[4,6-bis(dimethylamino)-1,3,5 -triazin-2-yl]-1, 1'-bi-2-naphthol (R)-2 and 2,4-bis(2,2'-dihydroxy-1,1'-binaphthalen-3-yl)-6-(ptolyl)-1,3,5-triazine (R,R)-3 have been obtained by directed ortho-lithiation or Suzuki cross-coupling process. Ligand (R)-1 shows improved catalytic properties for the asymmetric diethylzinc addition to aromatic aldehydes. (c) 2005 Elsevier Ltd. All rights reserved.