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Enantioselektive Synthese von α‐substituierten N ‐Methyl‐sulfonamiden. Vorläufige Mitteilung
Author(s) -
Enders Dieter,
Thomas Christian R.,
Raabe Gerhard,
Runsink Jan
Publication year - 1998
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19980810543
Subject(s) - chemistry , racemization , moiety , amine gas treating , enantiomer , hydrolysis , stereochemistry , medicinal chemistry , chirality (physics) , organic chemistry , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark
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 ( Scheme 1 ).