Enzymatic resolution of (±)-2-endo-hydroxymethyl and acetoxymethyl substituted hexachloronorbornene derivatives

Article abstract of DOI:10.1016/j.tetasy.2005.06.014

(±)-2-endo-Hydroxymethyl-1,4,5,6,7,7-hexachlorobicyclo[2.2.1] hept-5-ene and (±)-2-endo-acetoxymethyl-1,4,5,6,7,7-hexachlorobicyclo[2. 2.1]hept-5-ene were resolved by using various hydrolases to afford enantiomerically enriched products with ees of 94-98%. The absolute configuration was determined by transforming 2-endo-acetoxymethyl-1,4,5,6,7,7- hexachlorobicyclo[2.2.1]hept-5-ene into 2-endo-hydroxymethyl-bicyclo[2.2.1]hept- 5-ene with known absolute configuration.