DOI: 10.1002/anie.200460236. Highly Enantioselective Iron‐Catalyzed Sulfide Oxidation with Aqueous Hydrogen Peroxide under Simple Reaction Conditions

Highly Enantioselective Iron‐Catalyzed Sulfide Oxidation with Aqueous Hydrogen Peroxide under Simple Reaction Conditions

10.1002/anie.200460236

Crossref journal-article

Wiley

Angewandte Chemie International Edition (311)

Bibliography

Legros, J., & Bolm, C. (2004). Highly Enantioselective IronâCatalyzed Sulfide Oxidation with Aqueous Hydrogen Peroxide under Simple Reaction Conditions. Angewandte Chemie International Edition, 43(32), 4225â4228. Portico.

Authors 2

Julien Legros (first)
Carsten Bolm (additional)

References 42 Referenced 231

{'key': 'e_1_2_3_1_2', 'first-page': '767', 'volume-title': 'Anorganische Chemie', 'author': 'Cotton F. A.', 'year': '1982'} / Anorganische Chemie by Cotton F. A. (1982)
For reviews on non‐heme iron catalysts in oxidation reactions see:
10.1016/S0010-8545(98)00119-2
10.1016/S0010-8545(00)00320-9
For overviews on the use of hydrogen peroxide in oxidation reactions see:
{'key': 'e_1_2_3_6_2', 'volume-title': 'Catalytic Oxidations with Hydrogen Peroxide as Oxidant', 'year': '1992'} / Catalytic Oxidations with Hydrogen Peroxide as Oxidant (1992)
10.1039/9781847550132 / Applications of Hydrogen Peroxides and Derivatives by Jones C. W. (1999)
10.1021/cr020471z
10.1039/b303160h
For reviews on asymmetric sulfoxidations see:
10.1002/9783527619399.ch5m
10.1002/0471721506.ch10
{'key': 'e_1_2_3_13_2', 'first-page': '697', 'volume-title': 'Comprehensive Asymmetric Catalysis', 'author': 'Bolm C.', 'year': '1999'} / Comprehensive Asymmetric Catalysis by Bolm C. (1999)
10.1021/cr990372u
10.1021/cen-v081n047.p019
For other iron‐catalyzed sulfoxidations see:
10.1021/jo00298a046
10.1039/C39900001378
10.1016/S0957-4166(00)86106-6
10.1039/c39920000254
10.1016/0304-5102(92)80030-K
10.1016/S0040-4039(97)00710-7
10.1021/ic980958j
10.1002/1521-3765(20020301)8:5<1196::AID-CHEM1196>3.0.CO;2-Z
10.1002/ange.200352635
10.1002/anie.200352635
Schiff bases of this type have also been used in vanadium‐catalyzed asymmetric sulfide oxidations with H2O2. Most interestingly the same ligand3(derived from 3 5‐di‐iodosalicyladehyde) that is optimal for the V‐catalyzed asymmetric sulfur oxidation is also optimal in the iron‐promoted process. For the vanadium‐catalyzed reaction see:
10.1002/ange.19951072317
10.1002/anie.199526401
10.1016/S1381-1169(96)00359-7
10.1055/s-1998-1948
10.1055/s-2002-32582
10.1021/jo0205560
10.1021/ol034254b
10.1016/S0010-8545(02)00249-7
10.1002/(SICI)1521-3757(19990601)111:11<1672::AID-ANGE1672>3.0.CO;2-2
10.1002/(SICI)1521-3773(19990601)38:11<1570::AID-ANIE1570>3.0.CO;2-Y
10.1055/s-2002-19361
10.1021/ja015884g
Sodium potassium cesium and tetrabutyl ammonium salts have also been assessed in the oxidation of2 a:ANa4 90 %ee;AK4 88 %ee;ACs4 87 %ee;ABu4N4 82 %ee.
In oxidations that give sulfoxides with higheevalues (≥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 inherenteevalue 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.
10.1021/cr020622y

Dates

Type	When
Created	21 years ago (Aug. 9, 2004, 6:49 p.m.)
Deposited	1 year, 10 months ago (Oct. 10, 2023, 4:03 p.m.)
Indexed	2 weeks, 4 days ago (Aug. 5, 2025, 8:42 a.m.)
Issued	21 years ago (Aug. 9, 2004)
Published	21 years ago (Aug. 9, 2004)
Published Online	21 years ago (Aug. 9, 2004)
Published Print	21 years ago (Aug. 13, 2004)

Funders 0

None

BibTeX

@article{Legros_2004, title={Highly Enantioselective Iron‐Catalyzed Sulfide Oxidation with Aqueous Hydrogen Peroxide under Simple Reaction Conditions}, volume={43}, ISSN={1521-3773}, url={http://dx.doi.org/10.1002/anie.200460236}, DOI={10.1002/anie.200460236}, number={32}, journal={Angewandte Chemie International Edition}, publisher={Wiley}, author={Legros, Julien and Bolm, Carsten}, year={2004}, month=aug, pages={4225–4228} }

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