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Pd(0)-Catalyzed Intramolecular Reductive Heck Reaction of Vinyl Iodide and Oxime Ether: Enantioselective Synthesis of Cyclic Allylic N-Alkoxy Amine.

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Whereas the intramolecular reductive Heck reaction of aryl/vinyl halide and alkene has been well documented, the oxime analogue remains extremely elusive. Herein we report the Pd(0)-catalyzed intramolecular reductive Heck reaction… Click to show full abstract

Whereas the intramolecular reductive Heck reaction of aryl/vinyl halide and alkene has been well documented, the oxime analogue remains extremely elusive. Herein we report the Pd(0)-catalyzed intramolecular reductive Heck reaction of vinyl iodide and oxime ether with the use of formic acid as the reductant. It is found that the TsOH additive plays a crucial role in the reaction efficiency, and the (S)-SEGPhos ligand enables cyclic allylic N-alkoxy amine products with high enantioselectivity.

Keywords: reductive heck; reaction; intramolecular reductive; heck reaction; vinyl

Journal Title: Organic letters
Year Published: 2022

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