Synthesis of enantiomerically pure 2-dimethylamino-2'-di(p-tolyl)stibano-1,1'-binaphthyl(MASb) and 2-diphenylphosphino-2'-di(p-tolyl)stibano-1,1'-binaphthyl (BINAPSb) and its evaluation for asymmetric reactions

Abstract

We are interested in the synthesis and utilization of optically active organoantimony compounds for asymmetric reaction as chiral ligands. We have recently reported that optically active 2,2'-bis[di-(p-tolyl)stibano-1,1'-binaphthyls (BINASb), is an useful ligand in palladium-catalyzed asymmetric allylic alkylation of racemic 1,3-diphenyl-2-propen-1-yl acetate. We present here the synthesis of enantiomerically pure 2-dimethylamino-2'-di(p-tolyl)stibano-1,1'-binaphthyl (MASb) and 2-diphenylphosphino-2'-di(p-tolyl)stibano-1,1'-binaphthyl (BINAPSb), and propose that they can be used as effective chiral ligands for palladium-catalyzed asymmetric reactions. Such as the allylic alkylation asymmetric hydrosilylation of stylene derivatives.