Highly enantioselective iron-catalyzed sulfide oxidation with aqueous hydrogen peroxide under simple reaction conditions

Angewandte Chemie - International Edition

Volumn 43, Issue 32, 2004, Pages 4225-4228

  Legros, Julien ^a   Bolm, Carsten ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

Asymmetric catalysis; Iron; Oxidation; Peroxides; Sulfoxides

Indexed keywords

CARBOXYLIC ACIDS; CATALYSIS; DERIVATIVES; HYDROGEN PEROXIDE; IRON; OXIDATION;

METAL-CATALYZED OXIDATION (MCO); TERMINAL OXIDANT;

SULFUR COMPOUNDS;

BENZOIC ACID; CARBOXYLIC ACID; HYDROGEN PEROXIDE; IRON; SULFIDE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION KINETICS; ENANTIOSELECTIVITY; EPOXIDATION; OXIDATION KINETICS; STEREOCHEMISTRY;

EID: 4644283019     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200460236     Document Type: Article

References (37)

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33. This strategy has already been demonstrated in asymmetric sulfoxidations: Maruyama and co-workers used 1-methylimidazole with iron porphyrin catalysts,[6b,c] and Katsuki and co-workers added methanol to Bolm's vanadium catalyst (C. Ohta, H. Shimizu, A. Kondo, T. Katsuki, Synlett 2002, 161-163). In both cases improvements in enantioselectivities were observed, whereas turnovers and yields did not increase. The use of those additives in the iron-catalyzed reaction shown in Scheme 1 had a negative effect.
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35. 4N4, 82% ee.
36. In oxidations that give sulfoxides with high ee values (≥ 90%) significant amounts of sulfone (ca. 15%) were detected in the crude product. Preliminary studies revealed the existence of a kinetic resolution process that enhances the inherent ee value of the sulfoxide. This behavior contrasts that found in the original process (without an additive[7]). Details of these findings will be reported in due course.
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