Enantioselective electrocatalytic oxidation of racemic sec-alcohols using a chiral 1-azaspiro[5.5]undecane-N-oxyl radical

Tetrahedron Letters

Volumn 40, Issue 35, 1999, Pages 6469-6472

  Kashiwagi, Yoshitomo ^a   Kurashima, Futoshi ^a   Kikuchi, Chikara ^a   Anzai, Jun ichi ^a   Osa, Tetsuo ^a   Bobbitt, James M ^a,b  

^a TOHOKU UNIVERSITY   (Japan)

^b UNIVERSITY OF CONNECTICUT   (United States)

Author keywords

Electrochemical reactions; Enantiomeric purity; Nitoxides; Resolution

Indexed keywords

4 ACETYLAMINO 2,2,7 TRIMETHYL 10 ISOPROPYL 1 AZASPIRO[5.5] UNDECANE N OXYL DERIVATIVE; ALCOHOL; NITROXYL RADICAL; RADICAL; UNCLASSIFIED DRUG;

ALCOHOL OXIDATION; ARTICLE; CYCLIC POTENTIOMETRY; ELECTROCHEMICAL ANALYSIS; ELECTROLYSIS; ORGANIC CHEMISTRY; OXIDATION REDUCTION REACTION; RACEMIC MIXTURE; REACTION ANALYSIS;

EID: 0033609758     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01325-8     Document Type: Article

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9. 3CN). Cyclic potential sweeps were generated by Hokuto Denko Model HAB-151 potentiostat/galvanostat. Cyclic voltammograms were recorded on a Graphtec Model WX1200 X-Y recorder. All electrochemical measurements were carried out at room temperature (ca. 20°C)
10. -1 flow rate, and detected by UV absorption at 254 nm.
11. S = ln[(l-C)(l-ee)]/ln[(l-C)(l+ee)] where ee is the fractional enantiomeric excess and C is the conversion. For an excellent discussion of kinetic resolutions see: Kagan, H. B.; Fiaund, J. C. Top. Stereochem., 1988, 18, 249.