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Transition Metal Catalyzed Asymmetric Oxidation of Sulfides Review

Journal Current Organic Chemistry
ISSN: 1385-2728 , E-ISSN: 1875-5348
Output data Year: 2008, Volume: 12, Number: 5, Pages: 386-404 Pages count : 19 DOI: 10.2174/138527208783743660
Tags HIGHLY ENANTIOSELECTIVE OXIDATION; ALKYL ARYL SULFIDES; HYDROGEN-PEROXIDE; KINETIC RESOLUTION; TITANIUM COMPLEXES; CHIRAL SULFOXIDES; IRON COMPLEXES; INHIBITORY-ACTIVITY; LIGANDS; MECHANISM
Authors Bryliakov Konstantin P. 1 , Talsi Evgenii P. 1
Affiliations
1 Boreskov Institute of Catalysis, Siberian Branch of the Russian Academy of Sciences, 630090, Pr. Lavrentieva 5, Novosibirsk, Russian Federation

Abstract: In the past two decades, chiral sulfoxides have been finding increasing use, reflecting growing interest both in convenient auxiliaries in asymmetric synthesis and products with biological properties containing a chiral sulfinyl group. In 1984, groups of Kagan and Modena discovered that titanium(IV) isopropoxide - diethyltartrate based systems (also known as “modified Katsuki-Sharpless reagents”) are capable of asymmetric oxidizing of prochiral sulfides by alkylhydroperoxides. Later, catalytic versions of the titanium tartrate systems were developed (with up to 90 % yield and 90 % ee for certain sulfides) that remain the most applied systems for asymmetric sulfoxidations. However, the low turnover numbers (5-20), complexity and expensiveness of such systems stimulated the search for other transition metal based catalytic systems. This review will cover the progress in transition metal catalyzed asymmetric sulfides oxidations achieved since the discoveries of early 1980s to the present days.
Cite: Bryliakov K.P. , Talsi E.P.
Transition Metal Catalyzed Asymmetric Oxidation of Sulfides
Current Organic Chemistry. 2008. V.12. N5. P.386-404. DOI: 10.2174/138527208783743660 WOS Scopus РИНЦ ANCAN OpenAlex
Dates:
Published print: Mar 1, 2008
Identifiers:
Web of science: WOS:000254038500004
Scopus: 2-s2.0-42049121685
Elibrary: 13588820
Chemical Abstracts: 2008:748065
Chemical Abstracts (print): 149:513709
OpenAlex: W2951561770
Citing:
DB Citing
Web of science 40
Scopus 44
Elibrary 43
OpenAlex 43
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