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d-Idose-Based Monoaza-15-Crown-5 Lariat Ethers: Synthesis of an Elusive d-Hexose and Application of Derived Macrocycles in Enantioselective Syntheses.
- Source :
-
Symmetry (20738994) . Sep2023, Vol. 15 Issue 9, p1714. 23p. - Publication Year :
- 2023
-
Abstract
- Carbohydrate-based macrocycles can be enantioselective catalysts in certain reactions. Previously, it was proven that the carbohydrate moiety could affect the catalytic activity of the monoaza-15-crown-5 type macrocycles derived from sugars. According to our experiments so far, the most effective enantioselective catalysts were the d-glucose- and the d-galactose-based crown ethers. To obtain more information about the effect of the carbohydrate unit, a rare monosaccharide, d-idose was incorporated into the monoaza-15-crown-5 structure. The key intermediates were methyl 4,6-O-benzylidene-α-d-idopyranoside and methyl 4,6-O-benzylidene-β-d-idopyranoside, which were synthesized from d-galactose. The efficiency of the idopyranoside-based crown compounds synthesized was investigated in asymmetric phase transfer reactions. In liquid-liquid biphasic reactions the highest enantioselectivity was 81% ee, while in solid-liquid phase systems the highest asymmetric induction was 67% ee. It was observed that the enantiodiscrimination was strongly dependent on the configuration of the anomeric center, on the side arm of the nitrogen, and on the structure of the substrate. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 20738994
- Volume :
- 15
- Issue :
- 9
- Database :
- Academic Search Index
- Journal :
- Symmetry (20738994)
- Publication Type :
- Academic Journal
- Accession number :
- 172753802
- Full Text :
- https://doi.org/10.3390/sym15091714