Asymmetric synthesis of amino acids by catalytic reduction of azlactones of substituted acylaminoacrylic acids

Autor: Khatskevich, I. É., Kalnin', I. K., Karpeiskaya, E. I., Klabunovskii, E. I.
Zdroj: Russian Chemical Bulletin; February 1983, Vol. 32 Issue: 2 p330-335, 6p
Abstrakt: Conclusions 1.It was found that SS-4-sec-butyl-5-oxazolones readily undergo epimerization. The ratio between the epimers was determined. The kinetics of epimerization and aminolysis under the action of a-phenylethylamine were studied.2.The aminolysis of SS-4-sec-butyl-5-oxazolones in tert-butanol proceeds by the reaction of neutral oxazolone molecules with the amine, and leads to preferential formation of the SSS-amide.3.The aminolysis of SS-4-sec-butyloxazolone in dimethoxyethane proceeds by the reaction of chiral carbanion with S-a-phenylethylammonium, with preferential formation of SRS-amide.4.A method for the reductive aminolysis of 4-sec-butylidene-5-oxazolones has been proposed.
Databáze: Supplemental Index
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