Enantioselective Synthesis of Diverse Sulfinamides and Sulfinylferrocenes from Phenylglycine-Derived Chiral Sulfinyl Transfer Agent

A new chiral sulfinyl transfer auxiliary derived from readily available phenylglycine was developed. This auxiliary is utilized to synthesize a diverse array of alkyl- and arylsulfinamides and sulfinylferrocenes in high yields and excellent ee's. The desired products are produced in a one-pot sequence from the oxathiazolidine 2-oxide by two sequential nucleophilic additions that proceed in a stereospecific manner.