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Novel resolution of chiral lactams
Author(s) -
Ürögdi László,
Kisfaludy Lajos,
Patthy Ágnes,
Vezér Csilla
Publication year - 1989
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570260124
Subject(s) - aminolysis , chemistry , lactam , enantiomer , optically active , derivative (finance) , resolution (logic) , organic chemistry , combinatorial chemistry , chiral auxiliary , stereochemistry , enantioselective synthesis , catalysis , artificial intelligence , computer science , financial economics , economics
Abstract A practical method of resolving chiral lactams, e.g. 1 , has been evolved, based on the hydroxymethylation of the lactam, followed by esterification of the product 2 with an optically active N ‐protected amino acid derivative, e.g. N ‐benzyloxycarbonylphenylalanine pentafluorophenyl ester 3 . Chromatographic separation of the unreacted hydroxymethylated lactam 2 and the ester 4 and subsequent dehydroxymethylation of the former and aminolysis of the latter afforded pure enantiomer, ( R )‐ 1 and ( S )‐ 1 .