Abstract
Novel H8-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 (KR/KS = 9.8 ̃ 19.4) of 2b in imine formation with 1,2-amino alcohols are higher than those of 2a (KR/KS = 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).
Original language | English |
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Pages (from-to) | 1289-1294 |
Number of pages | 6 |
Journal | Bulletin of the Korean Chemical Society |
Volume | 31 |
Issue number | 5 |
DOIs | |
State | Published - 20 May 2010 |
Keywords
- Amino acid
- Amino alcohol
- Chirality conversion
- Enantioselective recognition
- Octahydrobinaphthol