Zinc(II)-Chloride Induced Thioalkylation of Aluminium Enolates : Enantioselective Synthesis of Estradiol-3-Methyl-17-tert-Butyl Diether

Zinc(II)-chloride induced thioalkylation of the aluminium enolate 6 generated by conlugate reduction of the enone 5 leads - directly or via its trimethylsilylenol ether 6 - to alkylated hydrindanones 10 which are important intermediates in the synthesis of 19-norsteroids such as the title compound estradiol-3-methyl-17-tert-butyl diether 1