The first organocatalytic highly enantioselective reactions of substituted alpha-cyanoacetates and beta-dicarbonyl compounds with azodicarboxylates are reported. In the presence of 0.1-5 mol % of a quinidine-derived alkaloid beta-ICD, optically active quaternary hydrazine adducts are obtained in very high yields and with enantioselectivities up to >98% ee. A two-step procedure for the cleavage of the hydrazine N-N bond using SmI2 is also demonstrated.
Asymmetric construction of quaternary stereocenters by direct organocatalytic amination of alpha-substituted alpha-cyanoacetates and beta-dicarbonyl compounds / S., Saaby; Bella, Marco; K. A., Jorgensen. - In: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY. - ISSN 0002-7863. - STAMPA. - 126:26(2004), pp. 8120-8121. [10.1021/ja047704j]
Asymmetric construction of quaternary stereocenters by direct organocatalytic amination of alpha-substituted alpha-cyanoacetates and beta-dicarbonyl compounds.
BELLA, Marco;
2004
Abstract
The first organocatalytic highly enantioselective reactions of substituted alpha-cyanoacetates and beta-dicarbonyl compounds with azodicarboxylates are reported. In the presence of 0.1-5 mol % of a quinidine-derived alkaloid beta-ICD, optically active quaternary hydrazine adducts are obtained in very high yields and with enantioselectivities up to >98% ee. A two-step procedure for the cleavage of the hydrazine N-N bond using SmI2 is also demonstrated.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
