Synthesis and reactivities of enantiomerically pure beta-hydroxyalkyl and beta-aminoalkyl ferrocenyl sulfides

Enantiomerically pure beta-hydroxyalkyl and beta-aminoalkyl ferrocenyl sulfides have been synthesized in good yields from mercaptoferrocene and amino alcohol derivatives. Primary beta-aminoalkyl sulfides allowed the synthesis of tetrahydro-1,4-thiazepines containing the ferrocene moiety with good diastereoselectivity and -iminoalkyl sulfides. Some of these derivatives have successfully been employed as ligands for palladium-catalyzed allylic substitution, with asymmetric induction of up to 99% ee