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Communication | Regular issue | Vol 12, No. 10, 1979, pp.1305-1310
Published online, 1st January, 1970
DOI: 10.3987/R-1979-10-1305
Enantioselective Thiolysis of α-Amino Acid p-Nitrophenyl Ester Salts by Thiol-bearing Chiral Crown Ethers

Shigeki Sasaki and Kenji Koga*

*Faculty of Pharmaceutical Sciences, University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113, Japan

Abstract

Studies have been made on the design, synthesis, and test of thiol-bearing chiral crown ethers that work enantioselectively in the thiolysis of α-amino acid ester salts. It is shown that crown ethers (3 and 4), prepared from (+)-(1R,2R,3S,4S)-camphane-2,3-diol (12) and (-)-(1R,2S,3R,4S)-camphane-2,3-diol (16) respectively, exhibit enantiomeric discrimination by a factor of 1.7-1.9 in the rates of p-nitrophenol release from alanine p-nitrophenyl ester salts.