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Tartaric Acid Amides by the Gabriel Route
Author(s) -
Villa Gonzalez Susana,
Carlsen Per
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700198
Subject(s) - chemistry , thionyl chloride , ketene , tartaric acid , ring (chemistry) , hydrolysis , salt (chemistry) , chloride , optically active , medicinal chemistry , ammonium , acyl chloride , ammonium chloride , organic chemistry , stereochemistry , citric acid
Optically active (3 R ,4 R )‐3,4‐diacetoxypyrrolidine‐2,5‐dione was prepared from L ‐tartaric acid by ring closure of the ammonium salt of (2 R ,3 R )‐2,3‐diacetoxy‐3‐carbamoylpropanoic acid with thionyl chloride. Mechanistic considerations indicate that the ring closure proceeds through two competing pathways: either direct ring closure of an intermediate acyl chloride or in a parallel route via a ketene intermediate. The cyclic product was further converted into the optically active tartramonoamides and tartradiamides by hydrolysis and reaction with appropriate alkylamines, respectively. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)