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Last years numerous excellent results were obtained in asymmetric catalysis using transition metal complexes with axial chiral monodentate phosphite ligands, derived from easily available diol (Ra)- or (Sa)-BINOL. However, in spite of a wide diversity of this reach collection, so far it has been limited by structures of a pure axial chirality or by those combining elements of axial and exo-cyclic C*-central chirality. Our research was aimed at the preparation of (i) the first optically active phosphite ligands bearing two such powerful elements of the chirality as axial and planar one, and (ii) further transformation of these ligands into corresponding phosphapalladacycles of a new structural and stereochemical type. The equimolecular mixture of two phosphite’s diastereomers, (Sa,Spl)-HL and (Sa,Rpl)- HL, was obtained by standard methods using commercially available diol (Sa)-BINOL and 4-hydroxy-[2.2]paracyclophane (рСр). One of the diastereomers was isolated in a stereochemically pure form by means of their 1:1 mixture crystallization (31P NMR data). Several approaches to the C–H bond activation have been aprobated for the target palladacycle preparation.