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Updated: Feb 12, 2026

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
Complex Hydroindoles by an Intramolecular Nitrile-Intercepted Allylic Alkylation Cascade Reaction
Peter Vertesaljai1, Ion Ghiviriga1, Alexander J Grenning1
1Department of Chemistry , University of Florida , P.O. Box 117200, Gainesville , Florida 32611 , United States.
Abstract:
Bisnucleophilic reagents derived from malononitrile, ketones, benzaldehydes, and nitromethane can react with bisallylic electrophiles via a nitrile-intercepted allylic alkylation cascade reaction to yield complex hydroindole architectures. Also noteworthy is that the only stoichiometric byproducts from the preparation and reaction of the bisnucleophile and biselectrophile are water, acetic acid, and bicarbonate, making it a potentially "green" platform for multistep complex molecule synthesis. These scaffolds can be converted into hydrooxindoles by a unique olefin isomerization followed by Witkop-Winterfeldt-like oxidation.
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