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Asymmetric Vinylogous Diels–Alder Reactions Catalyzed by a Chiral Phosphoric Acid
Author(s) -
Tian Xu,
Hofmann Nora,
Melchiorre Paolo
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201310487
Subject(s) - cycloaddition , chemoselectivity , phosphoric acid , diels–alder reaction , reactivity (psychology) , catalysis , chemistry , organic chemistry , diene , combinatorial chemistry , medicine , alternative medicine , pathology , natural rubber
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.