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Chiral amides via copper-catalysed enantioselective conjugate addition

Schoonen, Anne K.; Angeles Fernandez-Ibanez, M.; Fananas-Mastral, Martin; Teichert, Johannes F.; Feringa, Ben L.

A highly enantioselective one pot procedure for the synthesis of β-substituted amides was developed starting from the corresponding α,β-unsaturated esters. This new methodology is based on the copper-catalysed enantioselective conjugate addition of Grignard reagents to α,β-unsaturated esters and subsequent direct formation of amides by quenching the corresponding enolates with different amines. Various primary and secondary amines bearing alkyl or aryl substituents can be used giving rise to a large variety of β-substituted amides with excellent enantioselectivities.
Published in: Organic & biomolecular chemistry : OBC, 10.1039/c3ob41923a, Royal Society of Chemistry
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  • This publication is with permission of the rights owner freely accessible due to an Alliance licence and a national licence (funded by the DFG, German Research Foundation) respectively.