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Updated: Feb 3, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Photocatalytic Three-Component Umpolung Synthesis of 1,3-Diamines
Thomas Rossolini1, Jamie A Leitch1, Rachel Grainger2
1Department of Chemistry , University of Oxford , Chemistry Research Laboratory, 12 Mansfield Road , Oxford OX1 3TA , United Kingdom.
Abstract:
A visible-light-mediated photocatalytic umpolung synthesis of 1,3-diamines from in situ-generated imines and dehydroalanine derivatives is described. Pivoting on a key nucleophilic addition of photocatalytically generated α-amino radicals to electron-deficient alkenes, this three-component coupling reaction affords 1,3-diamines efficiently and diastereoselectively. The mild protocol tolerates a wide variety of functionalities including heterocycles, pinacol boronates, and aliphatic chains. Application to biologically relevant α-amino-γ-lactam synthesis and extension to 1,3-aminoalcohols is also demonstrated.
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