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Updated: Jan 29, 2026

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
Photochemically Produced Aminocyclobutanes as Masked Dienes in Thermal Electrocyclic Cascade Reactions
Luke D Elliott1, Kevin I Booker-Milburn1
1School of Chemistry , University of Bristol , Cantock's Close , Bristol , BS8 1TS , U.K.
Abstract:
Cyclobutane products of a triplet sensitized enamide-alkene intramolecular [2 + 2] photocycloaddition have been shown to undergo fragmentation under acidic conditions. This lability has been exploited by inducing a complexity-generating thermal electrocyclic cascade sequence involving the in situ formation of a cyclobutene, followed by electrocyclic ring opening, Diels-Alder cycloaddition, and subsequent lactamization. This combination of excited state photochemistry and thermal electrocyclic cascade reactions allows simple planar molecules to be rapidly transformed into sp3-rich scaffolds.
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