The intermolecular a-allylation of enals and enones occurs by the condensation of variously substituted allen- amides with allylic alcohols. Cooperative catalysis by [Au- (ItBu)NTf2] and AgNTf2 enables the synthesis of a range of densely functionalized a-allylated enals, enones, and acyl silanes in good yield under mild reaction conditions. DFT calculations support the role of an a-gold(I) enal/enone as the active nucleophilic species.
Gold(I)-Assisted a-Allylation of Enals and Enones with Alcohols / Mastandrea, Marco Michele; Mellonie, Niall; Giacinto, Pietro; Collado, Alba; Nolan, Steven P.; Miscione, Gian Pietro; Bottoni, Andrea; Bandini, Marco. - In: ANGEWANDTE CHEMIE. INTERNATIONAL EDITION. - ISSN 1433-7851. - STAMPA. - 54:49(2015), pp. 14885-14889. [10.1002/anie.201507218]
Gold(I)-Assisted a-Allylation of Enals and Enones with Alcohols
GIACINTO, PIETRO;MISCIONE, GIAN PIETRO;BOTTONI, ANDREA;BANDINI, MARCO
2015
Abstract
The intermolecular a-allylation of enals and enones occurs by the condensation of variously substituted allen- amides with allylic alcohols. Cooperative catalysis by [Au- (ItBu)NTf2] and AgNTf2 enables the synthesis of a range of densely functionalized a-allylated enals, enones, and acyl silanes in good yield under mild reaction conditions. DFT calculations support the role of an a-gold(I) enal/enone as the active nucleophilic species.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
