Tartaric Acid Amides by the Gabriel Route

European Journal of Organic Chemistry - Tập 2007 Số 21 - Trang 3495-3502 - 2007
Susana V. González1, Per H. J. Carlsen1
1Department of Chemistry, Norwegian University of Science and Technology, 7491 Trondheim, Norway

Tóm tắt

AbstractOptically active (3R,4R)‐3,4‐diacetoxypyrrolidine‐2,5‐dione was prepared from L‐tartaric acid by ring closure of the ammonium salt of (2R,3R)‐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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