Synthetic and biotransformation studies on prochiral non-proteinogenic amino acids: Diethyl alpha-acetamido, alpha-alkylmalonates
UNSPECIFIED (2000) Synthetic and biotransformation studies on prochiral non-proteinogenic amino acids: Diethyl alpha-acetamido, alpha-alkylmalonates. INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 39 (1). pp. 10-15. ISSN 0376-4699Full text not available from this repository.
Nine diethyl alpha-acetamido, alpha-alkylmalonates 3-11 (alkyl=methyl, benzyl, 3-fluorobenzyl, 4-fluorobenzyl, 2,6-difluorobenzyl, 3-trifluoromethylbenzyl, 4-trifluoromethylbenzyl, 2-chlorobenzyl and 3-chlorobenzyl) have been synthesised in three steps starting with diethyl malonate in overall yields of 49-90%. The structures of C-alkylated acetamidomalonates have been established on the basis of their spectral data, the structures of two compounds 9 and 11 are also confirmed on the basis of their X-ray crystallographic studies. Further, the X-ray crystal structure of the chiral monoethyl ester of alpha-acetamidomalonic acid 1 has been studied. None of our C-alkylated acetamidomalonate has been found to be a substrate for lipase-catalysed enantiodifferentiating deesterification/ hydrolysis of the symmetric diester groups.
|Item Type:||Journal Article|
|Subjects:||Q Science > QD Chemistry|
|Journal or Publication Title:||INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY|
|Publisher:||NATL INST SCIENCE COMMUNICATION|
|Number of Pages:||6|
|Page Range:||pp. 10-15|
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