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Tartaric Acid Amides by the Gabriel Route

✍ Scribed by Susana Villa Gonzalez; Per Carlsen

Book ID: 102175445
Publisher: John Wiley and Sons
Year: 2007
Tongue: English
Weight: 151 KB
Volume: 2007
Category: Article
ISSN: 1434-193X
DOI: 10.1002/ejoc.200700198

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✦ Synopsis

Abstract

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)

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