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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Ru-Catalyzed Additive-Controlled Spirocyclization/Alkenylation of Benzimidates with 1,4-Naphthoquinone
Aritra Mukherjee1,2, Keshav Semwal1, Rahul Bangari1,2
1Department of Chemistry, IIT Dharwad, Permanent Campus, Chikka Malligwad, Dharwad, Karnataka 580007, India.
Abstract:
A selective Ru(II)-catalyzed spirocyclization of benzimidates with 1,4-naphthoquinone under oxidant-free conditions to afford three-dimensional spiro-isoindoline frameworks is reported. Simple variation of the additive enables divergent reactivity, selectively yielding spirocyclized or alkenylated ester products. The protocol is operationally simple and supports a telescopic process in which imidates are generated in situ from benzonitriles and used without isolation, by minimizing solvent waste. Substrate scope shows moderate to good reactivity, enabling combinatorial synthesis of diverse compounds.
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