Remote transmission: In the presence of chiral amines, 2,4-dienones are activated toward the attack of a nucleophile at the a position, a mode of activation that is termed vinylogous iminiuma ion catalysis. Specifically, the 1,6a addition of alkyl thiols to β-substituted cyclic dienones was catalyzed by a cinchona-based primary amine; the reaction was highly stereoselective and displayed high selectivity for reaction at the a position. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Aminocatalytic enantioselective 1,6a additions of alkyl thiols to cyclic dienones: Vinylogous iminiuma ion activation / Tian X.; Liu Y.; Melchiorre P.. - In: ANGEWANDTE CHEMIE. INTERNATIONAL EDITION. - ISSN 1433-7851. - ELETTRONICO. - 51:26(2012), pp. 6439-6442. [10.1002/anie.201202392]
Aminocatalytic enantioselective 1,6a additions of alkyl thiols to cyclic dienones: Vinylogous iminiuma ion activation
Melchiorre P.
Ultimo
Supervision
2012
Abstract
Remote transmission: In the presence of chiral amines, 2,4-dienones are activated toward the attack of a nucleophile at the a position, a mode of activation that is termed vinylogous iminiuma ion catalysis. Specifically, the 1,6a addition of alkyl thiols to β-substituted cyclic dienones was catalyzed by a cinchona-based primary amine; the reaction was highly stereoselective and displayed high selectivity for reaction at the a position. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.