Synthesis and resolution of axially chiral C2-symmetric 1,1'-binaphthyl-substituted tetramethylethylenediamines

Article abstract of DOI:10.1016/S0957-4166(97)00301-7

The axially chiral TMEDA derivatives 1 and 2 in which tetramethylethylenediamine is substituted respectively by one and two 1,1'-binaphthyl units at their 2,2'-positions, are of interest as chiral catalysts. Experimental details of their preparation in enantiomerically pure form are given. Two different routes have been followed, involving alkylation of both N,N-dimethyl ethylenediamine and ethylenediamine by 2,2'-bis-(bromomethyl)-1,1'-binaphthyl either enantiomerically pure as prepared from resolved 1,1'-binaphthyl-2,2'-dicarboxylic acid or racemic, the resulting racemic diamines 1 and 2 being then resolved with dibenzoyl-tartaric acid.