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Alonso AM, Horcajada R, Motevalli M, et al. The reactivity, as electrogenerated bases, of chiral and achiral phenazine radical-anions, including application in asymmetric deprotonation. Org Biomol Chem. 2005;3(15):2842-7doi: 10.1039/b506309d.
Alonso, A. M., Horcajada, R., Motevalli, M., Utley, J. H., & Wyatt, P. B. (2005). The reactivity, as electrogenerated bases, of chiral and achiral phenazine radical-anions, including application in asymmetric deprotonation. Organic & biomolecular chemistry, 3(15), 2842-7. https://doi.org/10.1039/b506309d
Alonso, A Mateo, et al. "The reactivity, as electrogenerated bases, of chiral and achiral phenazine radical-anions, including application in asymmetric deprotonation." Organic & biomolecular chemistry vol. 3,15 (2005): 2842-7. doi: https://doi.org/10.1039/b506309d
Alonso AM, Horcajada R, Motevalli M, Utley JH, Wyatt PB. The reactivity, as electrogenerated bases, of chiral and achiral phenazine radical-anions, including application in asymmetric deprotonation. Org Biomol Chem. 2005 Aug 07;3(15):2842-7. doi: 10.1039/b506309d. Epub 2005 Jul 01. PMID: 16032362.
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Org Biomol Chem. 2005 Aug 07;3(15):2842-7. doi: 10.1039/b506309d. Epub 2005 Jul 01.

The reactivity, as electrogenerated bases, of chiral and achiral phenazine radical-anions, including application in asymmetric deprotonation.

Organic & biomolecular chemistry

A Mateo Alonso, Roberto Horcajada, Majid Motevalli, James H P Utley, Peter B Wyatt

Affiliations

  1. Department of Chemistry, Queen Mary, University of London, Mile End Road, London, UK E1 4NS.

PMID: 16032362 DOI: 10.1039/b506309d

Abstract

Radical-anions, electrochemically generated in aprotic solvent from C(2) symmetric homochiral phenazine derivatives, act as chiral electrogenerated bases (EGBs) in the desymmetrisation by selective deprotonation of a prochiral epoxide (3,4-epoxy-2,3,4,5-tetrahydrothiophene-1,1-dioxide); the anion produced is trapped by mesitoic anhydride. The phenazines may be recovered in high yield by air oxidation. Enantiomeric excesses are modest (8-34%) but this is to our knowledge the first demonstration of such stereoselective electrochemically-initiated deprotonation. The reactivity of phenazine radical-anions as EGBs has also been explored by measurements of the rates of proton transfer; the prochiral epoxide was found to have a kinetic acidity similar to that of the methyltriphenylphosphonium cation.

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