154632-89-0Relevant academic research and scientific papers
An improved synthesis of aziridine-2,3-dicarboxylates via azido alcohols - Epimerization studies
Breuning, Alexander,Vicik, Radim,Schirmeister, Tanja
, p. 3301 - 3312 (2007/10/03)
The reasons for epimerization of 3-azido-2-hydroxysuccinates observed during the ring opening of epoxides or cyclic sulfites with sodium azide is now clarified. It is caused by the high acidity of the proton at the 3-position. This is proven by a proton deuterium exchange in assays with either D 2O or DCl containing solvents. The anti-3-azido-2-hydroxysuccinates serve as intermediates for enantiomerically pure trans-aziridine-2,3- dicarboxylates for which an optimized synthetic pathway is presented. The first example of an enantiomerically pure mixed diester of the aziridine-2,3- dicarboxylic acid the synthesis of the allyl ethyl ester is reported herein.
Candida cylindracea Lipase-Catalysed Hydrolysis of Methyl Aziridine-2-carboxylates and 2,3-dicarboxylates
Bucciarelli, Maria,Forni, Arrigo,Moretti, Irene,Prati, Fabio,Torre, Giovanni
, p. 3041 - 3046 (2007/10/02)
N-Substituted aziridine-2-carboxylates and 2,3-dicarboxylates have been resolved with good to excellent stereochemical purity by enzymatic hydrolysis catalysed by lipase from Candida cylindracea.
