New synthetic strategy to highly symmetric chiral macrocycles from carbohydrate derivatives
1989; Elsevier BV; Volume: 45; Issue: 11 Linguagem: Inglês
10.1016/s0040-4020(01)81039-5
ISSN1464-5416
AutoresCristina Vicent, Manuel Martín‐Lomas, Soledad Penadés,
Tópico(s)Molecular Sensors and Ion Detection
ResumoA simple strategy for the synthesis of highly symmetric macrocycles incorporating carbohydrates is presented. The application of this strategy to the synthesis of optically active tetra-gluco-24-crown-8 (1), bis-gluco-15-crown-5 (3), and bis-gluco-21-crown-8 (5) is described. Preliminary studies showed that macrocycles 1, 3 and 5 complex ammonium salts. These macrocyclic compounds have been used as catalysts in the asymmetric Michael addition of methyl α-phenylacetate to methyl acrylate.
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