Helvetica Chimica Acta p. 1329 - 1336 (1998)
Update date:2022-08-02
Topics:
Enders, Von Dieter
Thomas, Christian R.
Raabe, Gerhard
Runsink, Jan
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).
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