Enantioselective dihydroxylation of olefins by osmium tetroxide in the presence of an optically active 1,1'-binaphthyl diamine derivative

Article abstract of DOI:10.1016/0957-4166(96)00388-6

The chiral diamine (S)-1, introduced by Cram and Mazaleyrat, has been reprepared following a different sequence which involves the resolution of diacid (RS)-3. The e.e. (via HPLC and NMR), the absolute configuration (via CD) and the most stable conformation (via UV and molecular mechanics calculations) of (S)-1 have been determined. (S)-1 has been employed as a chiral auxiliary in the stoichiometric syn-dihydroxylation of olefins obtaining optically active 1,2-diols with e.e.s up to 98%.