期刊
ORGANIC & BIOMOLECULAR CHEMISTRY
卷 8, 期 8, 页码 1763-1768出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/b925367j
关键词
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资金
- Marie Curie European Reintegration [FP7-PEPLE-ERG-2008-239244]
- Spanish Direccion General de Investigacion, Ciencia y Tecnologia [CTQ-2005-074007BQU]
- Ministerio de Educacion y Ciencia (MEC)
Xanthone derivatives were tested as organocatalysts for the Michael addition of pyrrolidine to an alpha,beta-unsaturated lactam. The receptors combine a double H-bond donor pattern that resembles the oxyanion hole in natural enzymes, with a sulfone or sulfoxide that acts as a proton-transfer group. Since these compounds cannot be obtained enantiomerically pure from natural sources, chiral resolution was necessary to study their enantioselectivity. For the most promising receptor, this was accomplished using a new methodology that exploits its supramolecular interactions with a chiral guest and that is inspired in dynamic combinatorial chemistry. The success in the resolution of the racemic mixture indicates that this new method offers an alternative to kinetic resolution.
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