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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Direct Regioselective Reductive Allylation of Imines: Application to Synthesis of Oxazines with Halogenated Reagent
Tao Ju1, Ai-Ling Lu1, Yu-Chao Zhou1
1School of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou, 250002, P. R. China.
Abstract:
Oxazines are an important class of compounds in oxazine ligands and medical chemistry. Here, we describe a linear-selective allylation of imines with allyl electrophiles via cross-electrophile coupling reactions, followed by cyclization with halogenated reagents, providing a new strategy to afford oxazine compounds with a tetrasubstituted carbon center. Mechanistic studies indicate that α-amino carbanion, generated by successive single-electron transfer processes, is a key intermediate for nucleophile attack on π-allylpalladium in photoredox/palladium catalysis.
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