[Stereochemistry of the reductive amination of 4-oxoproline derivatives with glycine esters].
An amination of 4-oxoproline derivatives with glycine methyl or benzyl ester and sodium cyanoborohydride led to the mixtures of corresponding diastereomeric 4-cis- and 4-trans-glycinoproline derivatives. We found that the ratio of diastereomers mainly depends on the structure of 4-oxoproline ester groups and, to a lesser extent, on the structure of N-acyl substituents. The best results were achieved with tert-butyl ester group; it ensured good yields of the amination products and the greatest prevalence of 4-cis-isomers. The structure of ester group in glycine molecule only scarcely affected the resulting ratio of N-(N-benzyloxycarbonylglycyl)-4-glycinoprolines. The English version of the paper: Russian Journal of Bioorganic Chemistry, 2002, vol. 28, no. 6; see also http://www.maik.ru.
Elin
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EA
Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, ul. Miklukho-Maklaya 16/10, GSP Moscow, 117997 Russia.
Onoprienko
V V
VV
Miroshnikov
A I
AI
D000586:Amination; D004952:Esters; D005998:Glycine / Q000737:chemistry*; D010084:Oxidation-Reduction; D011392:Proline / Q000031:analogs & derivatives* / Q000737:chemistry*; D013237:Stereoisomerism
D004952:Esters; C036784:4-ketoproline; D011392:Proline; D005998:Glycine