Diastereoselective addition of redox active esters to azomethine imines by electrosynthesis

Thanks to metal- and catalyst-free electrochemical conditions in an undivided cell, a series of readily available redox-active N -(acyloxy)phthalimide esters led to an efficient and highly stereoselective addition (85 : 15 to 95 : 5 dr) of putative radical species to chiral (racemic and enantioenric...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2022-05, Vol.58 (41), p.61-613
Hauptverfasser: Leleu, Ludovic, Martzel, Thomas, Fall, Arona, Sanselme, Morgane, Levacher, Vincent, Oudeyer, Sylvain, Brière, Jean-François
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Sprache:eng
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Zusammenfassung:Thanks to metal- and catalyst-free electrochemical conditions in an undivided cell, a series of readily available redox-active N -(acyloxy)phthalimide esters led to an efficient and highly stereoselective addition (85 : 15 to 95 : 5 dr) of putative radical species to chiral (racemic and enantioenriched) C5-substituted azomethine imines to provide an array of 31 polyaminated hydrazine derivatives as a single diastereoisomer. Highly stereoselective addition of electrogenerated putative radical species to chiral azomethine imines occurs upon SET cathodic reduction of redox-active N -(acyloxy)phthalimide esters.
ISSN:1359-7345
1364-548X
DOI:10.1039/d2cc01795d