Resolution and Absolute Configuration of Bicycloocta-2,6-diene-2-carboxylic Acid

Article abstract of DOI:10.1021/jo00161a012

An efficient resolution of the title acid (1) by using (+)- and (-)-α-phenethylamine is described.The (+) acid was determined to be 1S by chemical correlation through (+)-cis-bicyclo<3.3.0>octan-2-one (3) with (+)-cis-bicyclo<3.3.0>oct-7-en-endo-2-ol (4) where the absolute configuration is known to be 1R.The 1R configuration for (-)-3 was consistent with the negative Cotton effect observed for this ketone.