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Racemic 2--butylbutanedioic acid 4-t-butyl esters were synthesized from methyl hexanoate and t-butyl α-iodoacetate via alkylation and subsequently selective hydrolyzation. The (R)-and (S)-2-n-butylbutanedioic acid 4-t-butyl esters were obtained by the resolution of the above-mentioned racemic compounds with(S)-(-) or(R)-(+)-α-methylbenzylamine, respectively. The e.e. values of the two optical active products were determined to be above 99% by HPLC after the formation of two pairs of diastereoisomers with(R)-(+)-α-methylbenzylamine and(S)-phenylalanine methyl ester.
Racemic 2-butylbutanedioic acid 4-t-butyl esters were synthesized via methyl hexanoate and t-butyl α-iodoacetate via alkylation and subsequent selective hydrolysis. The (R) -and (S) -butyl esters were obtained by the resolution of the above-mentioned racemic compounds with (S) - (-) or (R) - (+) - a-methylbenzylamine, respectively. The ee values of the two optical active products were determined to be above 99% by HPLC after the formation of two pairs of diastereoisomers with (R) - (+) - a-methylbenzylamine and (S) -phenylalanine methyl ester.