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Journal ArticleDOI

Organocatalytic Oxidation. Asymmetric Epoxidation of Olefins Catalyzed by Chiral Ketones and Iminium Salts

01 Jul 2008-Chemical Reviews (American Chemical Society)-Vol. 108, Iss: 9, pp 3958-3987
TL;DR: Ketones with an Attached Chiral Moiety, Chiral Iminium Salt-Catalyzed Epoxidation, and Other Carbohydrate-Based Catalysts 3976 2.8.2.
Abstract: 2.6.4. Other Carbohydrate-Based Catalysts 3976 2.7. Carbocyclic Ketones 3977 2.8. Ketones with an Attached Chiral Moiety 3979 3. Chiral Iminium Salt-Catalyzed Epoxidation 3979 3.
Citations
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Journal ArticleDOI
TL;DR: The present state of the art in the use of enzymes and microorganisms for catalytic oxidation and oxyfunctionalization chemistry is reviewed.

382 citations

Journal ArticleDOI
TL;DR: A critical review discusses the advances that have been made using both metal-based and organocatalytic homogeneous catalysts to produce epoxides using environmentally benign oxidants, especially hydrogen peroxide.
Abstract: There has been a recent drive to develop asymmetric catalytic methods to produce epoxides using environmentally benign oxidants, especially hydrogen peroxide. This critical review discusses the advances that have been made using both metal-based and organocatalytic homogeneous catalysts (142 references).

281 citations

Journal ArticleDOI
TL;DR: This work represents the first example of an enantioselective reagent-controlled chlorolactonization that approaches synthetically useful enantiOSElectivities.
Abstract: A reagent controlled organocatalytic enantioselective chlorolactonization reaction has been developed. Several 4-aryl pentenoic acids were cyclized in the presence of 0.1 equiv of (DHQD)2PHAL, employing various N-chlorinated hydantoins as the terminal chlorenium source. Ten examples are presented with selectivities ranging from 43 to 90% ee. This work represents the first example of an enantioselective reagent-controlled chlorolactonization that approaches synthetically useful enantioselectivities.

256 citations

Journal ArticleDOI
TL;DR: An overview of catalyst systems capable of conducting asymmetric oxygenative transformations of organic molecules and, in line with the major trend to sustainability, relying on green oxidants H2O2 and O2 as the ultimate oxygen source is given.
Abstract: The discovery of simple and efficient catalyst systems for the asymmetric oxofunctionalization of hydrocarbons is a challenging task of catalytic chemistry. In this paper, we give an overview of catalyst systems capable of conducting asymmetric oxygenative transformations of organic molecules and, in line with the major trend to sustainability, relying on green oxidants H2O2 and O2 as the ultimate oxygen source. The full historical period of asymmetric oxidation catalysis (1970 to the present day) is covered; both transition-metal-based and organocatalytic systems are considered. The focus of this review is the catalytic properties of the existing catalyst systems, in particular stereoselectivity, activity, efficiency, and synthetic outlook. At the same time, mechanistic peculiarities of stereoselective oxygen transfer are given attention.

253 citations

References
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Journal ArticleDOI
TL;DR: Metal Oxides Generated in Situ 2461 4.1.
Abstract: 3. Soluble Metal Oxides 2459 3.1. Polyoxometalates 2459 3.2. Peroxotungstates 2459 3.3. Peroxomolybdates 2460 3.4. Methyltrioxorhenium 2461 3.5. Other Metal Oxides 2461 4. Metal Oxides Generated in Situ 2461 4.1. Selenium and Arsenic Compounds 2461 4.2. Simple Metal Salts 2462 5. Coordination Complexes 2463 5.1. Manganese Porphyrins 2463 5.2. Iron Porphyrins 2464 5.3. Manganese Salen Complexes 2466 5.4. 1,4,7-Triazacyclononane (TACN) Complexes 2466 5.5. Iron and Manganese Pyridyl-Amine Complexes 2468

984 citations

Journal ArticleDOI
TL;DR: This paper presents results of aalysis experiment conducted at the Dalian Institute of Chemical Physics of Chinese Academy of Sciences (Dalian 116023) and Jingmen Technological College (Jingmen 448000) using gas chromatography for the recovery of Na6(CO3) from Na2SO4.
Abstract: Laboratory for Advanced Materials and New Catalysis, School of Chemistry and Materials Science, Hubei University, Wuhan 430062, China,Laboratory of Natural Gas Utilization and Applied Catalysis, Dalian Institute of Chemical Physics of Chinese Academy of Sciences, Dalian 116023,China, and Jingmen Technological College, Jingmen 448000, ChinaReceived June 30, 2004

864 citations

Journal ArticleDOI
TL;DR: Aqueous H2O2 is an ideal oxidant, when coupled with a tungstate complex and a quaternary ammonium hydrogensulfate as an acidic phase-transfer catalyst in an economically, technically, and environmentally satisfying manner.

849 citations