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Updated: May 3, 2026

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
Asymmetric vinylogous Diels-Alder reactions catalyzed by a chiral phosphoric acid
Xu Tian1, Nora Hofmann, Paolo Melchiorre
1ICIQ-Institute of Chemical Research of Catalonia, Avenida Països Catalans 16, 43007 Tarragona (Spain) http://www.iciq.es/portal/862/default.aspx.
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.
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