Stereoselective Access to Diverse Alkaloid-like Scaffolds via an Oxidation/Double-Mannich Reaction Sequence

Charlie Mikan, Joseph Watson, Ryan Walton, Paul Waddell, Jonathan Knowles*

*Corresponding author for this work

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Sequential oxidative cleavage and double-Mannich reactions enable the stereoselective conversion of simple norbornenes into complex alkaloid-like structures. The products undergo a wide range of derivatization reactions, including regioselective enol triflate formation/cross-coupling sequences and highly efficient conversion to an unusual tricyclic 8,5,5-fused lactam. Overall, the process represents a formal one-atom aza-ring expansion with concomitant bridging annulation, making it of interest for the broader derivatization of alkene feedstocks.
Original languageEnglish
Pages (from-to)5549–5553
Number of pages5
JournalOrganic Letters
Issue number26
Early online date21 Jun 2024
Publication statusPublished - 5 Jul 2024

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