Synthesis of (R,R) and (S,S) bicyclo[3.3.0]octane-2,6-dione interactions between non-conjugated chromophores

Article abstract of DOI:10.1016/S0957-4166(00)80469-3

Optically pure bicylo[3.3.0]octane-2,6-dione is easily obtained with a yield of 4 % for each enantiomer from 1,5-cyclooctadiene in 5 steps, by resolution of the intermediate diol with menthyloxyacetic acid. Its CD is 60 % larger than twice the CD of a corresponding monoketone indicating interactions between non-conjugated chromophores.