Chiral recognition in complexes of tertiary acetylenic alcohols and sparteine; mutual optical resolution by complex formation

Tertiary acetylenic alcohols have been resolved efficiently by complex formation with (–)-sparteine, and (±)-sparteine was resolved by complex formation with the optically active tertiary acetylenic alcohols; an X-ray structural study of the 1:1 complex of 1-(o-bromophenyl)-1-phenylprop-2-ynol (1d) and (–)-sparteine showed that two hydrogen bonds, CC–H ⋯ OH and OH ⋯ N, are important in formation of the complex.