Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 354, Issue 4, Pages 740-746Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201100636
Keywords
amino acids; Michael addition; nitroolefins; organocatalysis; thioureas
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Among the class of primary amine-thioureas based on tert-butyl esters of a-amino acids, the most efficient organocatalyst for difficult Michael reactions was identified. The derivative based on (S)-di-tert-butyl aspartate and (1R,2R)-diphenylethylenediamine provided the products of the reaction between aryl methyl ketones and nitroolefins in excellent yields and enantioselectivities. In addition, this new catalyst can be used at low catalyst loading (5 mol%). The utility of this methodology was highlighted by the efficient synthesis of (S)-baclofen, (R)-baclofen and (S)-phenibut.
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