ChemInform Abstract: Synthesis of (R,R) and (S,S) Bicyclo(3.3.0)octane-2,6-dione. Interactions Between Non-Conjugated Chromophores

Optically pure bicyclo[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.