Enantioselective reaction of alpha-thio carbanion derived from 1-phenyl-1-(phenylthio)-1-(tributylstannyl)methane with cis-bicyclo[3.3.0]octane-3,7-dione monoethylene ketals in the presence of bis(oxazoline)s gave products with high diastereoselectivity and with high enantioselectivity. The reaction of alpha-seleno carbanions derived from bis(phenylseleno)arylmethanes also showed high diastereoselectivity and enantioselectivity. Deprotection and subsequent stereospecific elimination afforded axially chiral cis-arylmethylenebicyclo[3.3.0] octanes with high enantioselectivity (up to 99% ee).