ENANTIOSELECTIVE SYNTHESIS OF ALPHA-SUBSTITUTED N-METHYL-SULFONAMIDES

The first asymmetric alpha-alkylations of lithiated sulfonamides beari ng the chirality information within the amine moiety under high asymme tric inductions (de 83-95%) are described. Racemization-free acidic hy drolysis led to the title compounds 11 in acceptable overall yields an d with high enantiomeric purity (ee 91-greater than or equal to 98%; S cheme 2). As a novel chiral auxiliary, the primary amine (S,S)- or (R, R)-2 was synthesized employing the classical Erlenmeyer phenylserine s ynthesis (Scheme 1).