Stereochemical studies of the electrolytic reactions of organic compounds. 25. Electroorganic reactions on organic electrodes. 6. Electrochemical asymmetric oxidation of unsymmetric sulfides to the corresponding chiral sulfoxides on poly(amino acid)-coated electrodes

Asymmetric heterogeneous carbene transfer catalyzed by optically active ruthenium spirobifluorenylporphyrin polymers

“…[32][33][34] Various chiral polymers, mainly polythiophene 35 and polypyrrole derivatives, 30,36 have been described for the preparation of chiral electrodes capable of enantioselective recognition or electrosyntheses. 37 Although catalytic asymmetric reactions with chiral electropolymers have given some satisfactory results, 38 in no case were the polymers removed from the electrode. We report herein the development of novel chiral electropolymers for asymmetric heterogeneous carbene transfer to olefins.…”

Synthesis of enantioenriched sulfoxides

“…Later work by Komori and Nonaka using a variety of poly (amino acid) coated platinum/graphite electrodes established that the best electrode was the L-valine coated electrode. 168 Using this electrode tert-butyl phenyl sulfoxide 166 was obtained in 45% yield and 93% ee. This compared very favorably to the Kagan 18 and Modena 19 oxidation methods which were being published at that time.…”

Main Chain Chiral-Conjugated Polymers

“…Table 2.3 summarizes the polymerization conditions, molecular weights (measured by GPC) and specific optical rotations for polymers 2.10a-c and 2.11a-c. All these polymers are soluble in organic solvents. The best conditions for the synthesis of these polymers involve the use of Pd(PPh 3 ) 4 and CuI for the coupling of monomer 2.12 with aryl iodides, which produces polymers 2.10c and 2.11c. As shown by polymers (R)-2.11a-c, the optical rotation of these chiral polymers increases with increasing molecular weight of the polymers.…”