Synthesis of Novel H 8 -Binaphthol-based Chiral Receptors and Their Applications in Enantioselective Recognition of 1,2-Amino alcohols and Chirality Conversion of L-Amino acids to D-Amino acids

Novel $H_8$-binaphthol-based chiral receptors appended with an uryl moiety (2a) and a guanidinium moiety (2b) have been designed and synthesized for the enantioselective recognition of 1,2-amino alcohols via reversible imine formation. The selectivities ($K_R/K_S$ = 9.8 ~ 19.4) of 2b in imine format...

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Bibliographic Details
Published inBulletin of the Korean Chemical Society Vol. 31; no. 5; pp. 1289 - 1294
Main Authors Jung, Hye-In, Nandhakumar, Raju, Yoon, Hoe-Jin, Lee, Sang-Gi, Kim, Kwan-Mook
Format Journal Article
LanguageKorean
Published 2010
Subjects
Octahydrobinaphthol
Chirality conversion
Amino acid
Amino alcohol
Enantioselective recognition
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Summary:Novel $H_8$-binaphthol-based chiral receptors appended with an uryl moiety (2a) and a guanidinium moiety (2b) have been designed and synthesized for the enantioselective recognition of 1,2-amino alcohols via reversible imine formation. The selectivities ($K_R/K_S$ = 9.8 ~ 19.4) of 2b in imine formation with 1,2-amino alcohols are higher than those of 2a ($K_R/K_S$ = 1.8 ~ 4.5). Similar efficiency trend have been observed in the conversion of L-amino acids to D-amino acids, i.e., the efficiency of the receptor 2b (D/L ratio: 4.3 ~ 10.1) is superior to 2a (D/L ratio: 4.0 ~ 8.7).
Bibliography:KISTI1.1003/JNL.JAKO201014752579258
ISSN:0253-2964
1229-5949