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1 article(s) from Gazzotti, Margherita

Stereoselective electrochemical intramolecular imino-pinacol reaction: a straightforward entry to enantiopure piperazines

Margherita Gazzotti,
Fabrizio Medici,
Valerio Chiroli,
Laura Raimondi,
Sergio Rossi and
Maurizio Benaglia

Beilstein J. Org. Chem. 2025, 21, 1897–1908, doi:10.3762/bjoc.21.147

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Scheme 1: Synthesis of vicinal diamines via imino-pinacol coupling in the presence of metal-based reductants.

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Scheme 2: Light-promoted imino-pinacol coupling for the synthesis of vicinal diamines.

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Scheme 3: Historical perspective on electrochemical imino-coupling protocols.

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Scheme 4: Stereoselective electroreductive intramolecular imino-pinacol reaction.

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Scheme 5: Scope of the imino-pinacol coupling reaction. Reaction conditions: GC electrodes, NEt₄BF₄ (2.6 equi...

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Figure 1: X-ray determined structure of chiral piperazine 2b.

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Scheme 6: Continuous flow synthesis of piperazine 2a. The yield was determined by ¹H NMR spectroscopy using 1...

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Scheme 7: Proposed reaction mechanism.

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Scheme 8: Cyclic voltammetry investigation. Cyclic voltammetry of a 0.325 M solution of Et₄NBF₄ in DMF (light...

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Published 12 Sep 2025

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