Enantioselective synthesis of α-substituted N-methyl-sulfonamides

Article abstract of DOI:10.1002/hlca.19980810543

The first asymmetric α-alkylations of lithiated sulfonamides bearing the chirality information within the amine moiety under high asymmetric inductions (de 83-95 %) are described. Racemization-free acidic hydrolysis led to the title compounds 11 in acceptable overall yields and with high enantiomeric purity (ee 91- ≤98%; Scheme 2). As a novel chiral auxiliary, the primary amine (S,S)- or (R,R)-2 was synthesized employing the classical Erlenmeyer phenylserine synthesis (Schone I).