An unprecedented way to extend the synthetic utility of the Diels-Alder reaction to include a vinylogous reactivity space is described. A commercially available chiral phosphoric acid catalyst effectively activates cyclic 2,4-dienones towards a vinylogous [4+2] cycloaddition with 2-vinylindoles, which leads to stereochemically dense tetrahydrocarbazoles. The reaction proceeds with a high level of remote stereocontrol and exclusive chemoselectivity for the more distant double bond of the dienone. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Tian X., Hofmann N., Melchiorre P. (2014). Asymmetric vinylogous diels-alder reactions catalyzed by a chiral phosphoric acid. ANGEWANDTE CHEMIE. INTERNATIONAL EDITION, 53(11), 2997-3000 [10.1002/anie.201310487].
Asymmetric vinylogous diels-alder reactions catalyzed by a chiral phosphoric acid
Melchiorre P.
Ultimo
Supervision
2014
Abstract
An unprecedented way to extend the synthetic utility of the Diels-Alder reaction to include a vinylogous reactivity space is described. A commercially available chiral phosphoric acid catalyst effectively activates cyclic 2,4-dienones towards a vinylogous [4+2] cycloaddition with 2-vinylindoles, which leads to stereochemically dense tetrahydrocarbazoles. The reaction proceeds with a high level of remote stereocontrol and exclusive chemoselectivity for the more distant double bond of the dienone. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
