Studies on the Resolution of Racemic Amino Acid Esters by a New Resolving Agent R (-)Thiazolidine-2-thione-4-carboxylic Acid

Abstract

Abstract: Amino acid esters were resolved by a new resolving agent R (-)thiazolidine-2-thione-4-carboxylic acid R (-)TTCA . The optically active R (-)TTCA amino acid ester salts 1a_1f, [α]_D²⁰=-30.40°～-42.70° and optically active amino acid esters 2a_2f(e.e.: 35.40%～75.80%) were obtained. When 1a_1f reacted with aqueous NaOH, optically active amino acid esters 3a_3f(e.e : 39.50%～69.10%) were separated. The basicity of the amino group of amino acid esters and the formation heats of ammonium salts of amino acid ester have been studied using semiempirical quantum chemistry PM3 methods.

Key words: R (-)Thiazolidine-2-thione-4-carboxylic acid, Resolution, Optically active amino acid esters, Electronic structure, Formation heat

CLC Number:

O626.2

TrendMD:

LI Ye-Zhi, GUO Chun-Xiao, LU Xiang-Yang, SHEN Li-Chun, HUNAG Hua-Min . Studies on the Resolution of Racemic Amino Acid Esters by a New Resolving Agent R (-)Thiazolidine-2-thione-4-carboxylic Acid[J]. Chem. J. Chinese Universities, 1998, 19(6): 885.

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Studies on the Resolution of Racemic Amino Acid Esters by a New Resolving Agent R (-)Thiazolidine-2-thione-4-carboxylic Acid

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