Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 349, Issue 13, Pages 2156-2166Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200700184
Keywords
amino acids; diamines; Michael addition; nitroolefins; salt catalysis
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The chiral functionalized salt catalysis, which differs from the known enzyme- and transition metal-based methods, has been successfully developed to carry out the Michael addition of ketones to nitroolefins. Chiral anion salt (type I), chiral cation salt (type II), or chiral anion-chiral cation salt (type III) could be expected to be remarkably effective catalysts and afford the corresponding chemically and optically pure Michael addition adducts. A primary amine group activating the ketone during salt catalysis was their obvious and common property. Based on preliminary experimental investigations and previous reports on primary amine catalysis, a reaction pathway via imine, enamine, iminium ion to imine was proposed.
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