Amarjit Singh, A. Prasad, W. Errington
Aug 1, 2000
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0
Influential Citations
2
Citations
Journal
ChemInform
Abstract
Nine diethyl a-acetamido, a-alkylmalonates 3-1 1 (alkyl=methyl, benzyl, 3-fluorobenzyl, 4-fluorobenzyl, 2,6difluorobenzyl, 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 1 1 are also confirmed on the basis of their X-ray crystallographic studies. Further, the X-ray crystal structure of the chiral monoethyl ester of a-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.