oxidation of silyl enol ethersoxidation of silyl enol ethers
13 Oxidation of Silyl Enol Ethers 13.1 Introduction A number of useful synthetic transformations are based on the selective oxidation of the electron rich C-C double bond of trimethylsilyl enol ethers. A series of -diketones were readily prepared by the nitroxyl-radical-catalyzed oxidation of silyl enol ethers using magnesium monoperoxyphthalate hexahydrate (MMPP6H) as the co-oxidant. Journal of Organometallic Chemistry 2003, 679 (1) , 32-42. DOI: 10.1021/JO00381A051 Corpus ID: 196999916; Oxidation of silyl enol ethers using 2-sulfonyloxaziridines. Enol silyl ethers can be cleaved with nucleophiles such as MeLi, LiNH 2 or R 4 N + F - to give reactive enolates. The Journal of Organic Chemistry 1999, 64 (16) , 5954-5957. https://doi.org/10.1021/jo990477x Saa Stankovi and, James H. Espenson. In the Saegusa-Ito oxidation certain silyl enol ethers are oxidized to enones with palladium(II) acetate.In the original publication equal amounts of palladium and 1,4-benzoquinone are used to achieve the reaction with the benzoquinone acting as a co-oxidant. ChemInform 10.1002/chin.199441170 Authors K C Nicolaou 1 . The oxidation of silyl enol ethers with mCPBA or DMDO to yield -hydroxy ketones was discovered in 1974 by Rubottom et al., and is commonly known as the Rubottom oxidation.36 Both aromatic and aliphatic silyl enol ethers can undergo this transformation smoothly. 4,5 Clearly, the success of this process hinges on the efficient generation of the hybrid aryl Pd-radical species (i) from aryl . Synthesis of silyl enol ethers and related compounds Recent Literature Various ionic liquids have been tested for the preparation of silyl enol ethers from aldehydes and ketones with (bistrimethylsilyl)acetamide (BSA). A diverse set of carbonyl compounds can be dehydrogenated with ease by using this method. Hypervalent iodine oxidation of various silyl enol ethers (aromatic, heteroaromatic, and aliphatic) using iodosobenzene-boron trifluoride diethyl ether-water provides a general and direct route for the -hydroxylation of ketones. DOI: 10.1021/JO00152A003 Corpus ID: 94926773; Oxidation of enol silyl ethers: preparation of aeginetolide, dihydroactinidiolide, and actinidiolide @article{Rubottom1983OxidationOE, title={Oxidation of enol silyl ethers: preparation of aeginetolide, dihydroactinidiolide, and actinidiolide}, author={George M. Rubottom and H. D. Jun. 49 Scheme 18. DOI: 10.1016/S0022-328X (03)00470-4. The intermediate is an oxo-allylpalladium complex.. Saegusa oxidation. The structures of 2-hydroxy-() and 3-hydroxy-acetylpyridine are discussed as well a its also known as Saegusa-Ito oxidation. Keywords Brandeis University. Abstract An efficient Pd-catalyzed amidation of silyl enol ethers to produce -ketoamides has been developed using carbon monoxide and sulfonyl azides. In one application, a dienone is synthesized in two steps from . Oxidation of Silyl Enol Ethers @inproceedings{Weber1983OxidationOS, title={Oxidation of Silyl Enol Ethers}, author={W. Weber}, year={1983} } W. Weber; Published 1983; Chemistry; A number of useful synthetic transformations are based on the selective oxidation of the electron rich C-C double bond of trimethylsilyl enol ethers. Although silyl enol ethers of aldehydes and ketones are the traditional substrates for the Rubottom oxidation, as mentioned above, silyl ketene acetals and bis (silyl acetals) can be oxidized to their -hydroxy ester or carboxylic acid derivatives using lead (IV) acetate or hypofluorous acid - acetonitrile (HOF-ACN). Oxidation of Silyl Enol Ethers and Related Enol Derivatives to , -Unsaturated Enones and Other Carbonyl Compounds Yoshihiko Ito, Yoshihiko Ito Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Sakyo-ku, Kyoto, 606-8501, Japan Search for more papers by this author Michinori Suginome, Oxidation of Silyl Enol Ethers William P. Weber Chapter 380 Accesses Part of the Reactivity and Structure Concepts in Organic Chemistry book series (REACTIVITY,volume 14) Abstract A number of useful synthetic transformations are based on the selective oxidation of the electron rich C-C double bond of trimethylsilyl enol ethers. For example, the oxidation of 1-ethoxy-1-octene with a stoichiometric amount of 35% H(2)O(2) in the presence of PCWP (0.5 mol %) in a mixed solv Saegusa Oxidation : silyl enol ether oxidation September 29, 2022 by Chemistry Guide The Saegusa oxidation is known for the regioselective introduction of the , carbon-carbon double bond to cyclic and acyclic ketones via the Pd-mediated oxidation of the corresponding silyl enol ether. Angewandte Chemie International Edition 2002, 41 (6) , 996-1000. Cyclic silyl enol ethers were converted into the corresponding alpha . For example, the oxidation of 1-ethoxy-1-octene with a stoichiometric amount of 35% H(2)O(2) in the presence of PCWP (0.5 mol %) in a mixed solvent of methanol and dichloromethane at room . The oxidation of silyl enol ethers 111 with palladium(n) acetate is a convenient nnethod for the preparation of synthetically useful 2,6-disubstituted 2,3-dihydro-4-pyridones 112 95TL(36)9449>. Jump to main content Jump to site search The oxidation of vinyl and silyl enol ethers with aqueous hydrogen peroxide was first achieved by the use of peroxotungstophosphate (PCWP) as the catalyst. A novel and efficient method for the preparation of 1,2-diketones is reported. . Several oxidants have been successfully applied to synthesize 1,4-diketones from silyl enol ethers, e.g. Sulfenylation [ edit] Reacting a silyl enol ether with PhSCl, a good and soft electrophile, provides a carbonyl compound sulfenylated at an alpha carbon. Cambridge University. Download Table | Photoinduced Pd-Cat. Silyl ethers. Oxidation of Silyl Ethers a from publication: Photoinduced Formation of Hybrid Aryl Pd-Radical Species Capable of 1,5-HAT: Selective Catalytic Oxidation of . and related compounds. The oxidation of silyl enol ethers with the osmium tetroxide-amine oxide combination also leads to a In the Saegusa-Ito oxidation, certain silyl enol ethers are oxidized to enones with palladium (II) acetate . Oxidation of silyl enol ethers The oxidation of silyl enol ethers 111 with palladium(n) acetate is a convenient nnethod for the preparation of synthetically useful 2,6-disubstituted 2,3-dihydro-4-pyridones 112 95TL(36)9449>. Silanols. The Saegusa-Ito oxidation is a chemical reaction used in organic chemistry.It was discovered in 1978 by Takeo Saegusa and Yoshihiko Ito as a method to introduce - unsaturation in carbonyl compounds. The oxidation of vinyl and silyl enol ethers with aqueous hydrogen peroxide was first achieved by the use of peroxotungstophosphate (PCWP) as the catalyst. Pd (OH) 2 /C-Mediated Selective Oxidation of Silyl Enol Ethers by tert -Butylhydroperoxide, a Useful Method for the Conversion of Ketones to ,-Enones or -Silyloxy-,-enones. The structures of 2-hydroxy-(8) and 3-hydroxy-acetylpyridine (9) are discussed as well as the scope and mechanism of the reaction. Oxidation, Ketones Abstract Pd (OH) 2 -catalyzed oxidation of silyl enol ethers by t -BuOOH gives either -silyloxy-,-enones or ,-enones in good yields depending on the base used. Yields have been strongly influenced by the nature of the cation of the ionic liquid. AgjO [201], Cu(OTf)2 [202], Pb(OAc)4 [203] and iodosobenzene/BFj EtjO [204]. 13.2 Preparation of a,/l-Unsaturated Ketones Several methods have been developed to regiospecifically convert trimethyl . Water-soluble derivatives of IBX, and polymer-based IBX, with additional advantages, have also been developed. Novel catalytic hydrogenolysis of silyl enol ethers by the use of acidic ruthenium dihydrogen complexes. The oxidation of silyl enol ethers with the osmium tetroxide-amine oxide combination also leads to a-hydroxyketones in generally good yields.147. Fast -oxyamination of stable enolates, silyl enol ethers, and in situ deprotonated dialkyl 2-oxoalkane phosphonates and diphenyl-2-oxoalkyl phosphine oxides was performed in the presence of [Ru(bpy) 3] 2+ (bpy = 2,2-bipyridyl) as a photocatalyst, 2,2,6,6-tetramethylpiperidine nitroxide (TEMPO), and visible light. DOI: 10.1016/S0022-0728(97)00597-4 Corpus ID: 95981732; Electrochemical oxidation of some enol silyl ethers; investigations on the reactivity of cyclizable cation-radicals @article{Audebert1998ElectrochemicalOO, title={Electrochemical oxidation of some enol silyl ethers; investigations on the reactivity of cyclizable cation-radicals}, author={Pierre Audebert and Maxime Roche and Henri Bekolo . Oxidation of Silyl Enol Ethers by Using IBX and IBXN-Oxide Complexes: A Mild and Selective Reaction for the Synthesis of Enones. Oxidative couplingof silyl enol ethersas a useful syntheticmethod for carbon-carbon bond formationhas been known for a long time. Abstract Hypervalent iodine oxidation of various silyl enol ethers (aromatic, heteroaromatic, and aliphatic) using iodosobenzene-boron trifluoride diethyl ether-water provides a general and direct route for the -hydroxylation of ketones. Abstract ,-Unsaturated carbonyl compounds can be prepared by the oxidation of trimethylsilyl enol ethers with IBX ( 1) or IBXMPO ( 2 ). Indeed, if a hybrid aryl Pd-radical complex i, capable of HAT and a subsequent -hydride elimination, could be generated (Scheme 1b), it would allow for a direct oxidation of silyl ethers (1) into silyl enols (2). They can also be used directly as weak nucleophiles with very reactive electrophiles such as carbonium ions, the halogens (Br 2, Cl 2, I 2) or pseudohalogens (PhSCl, PhSeCl, Cl-N=O). [27] Langer, P. Synthesis 2002, 441-59. The U.S. Department of Energy's Office of Scientific and Technical Information ChemInform Abstract: Reaction of Silyl Enol Ethers with Phosphite Using Hypervalent Iodine Compound: A New Synthesis of 2-Aryl-2-oxoalkylphosphonates. Oxidation of silyl enol ethers by using IBX and IBX.N-oxide complexes: a mild and selective reaction for the synthesis of enones Angew Chem Int Ed Engl. Dehomologation of Aldehydes via Oxidative Cleavage of Silyl Enol Ethers with Aqueous Hydrogen Peroxide Catalyzed by Cetylpyridinium Peroxotungstophosphate under Two-Phase Conditions. 2002 Mar 15;41(6):996-1000. doi: 10.1002/1521-3773(20020315)41:6<996::aid-anie996>3..co;2-i. The oxidation of acyclic silyl enol ethers such as 1-[(trimethylsilyl)oxy]-1-octene under these conditions gave 1-hydroxy-2-octanone in 72% yield, while the same oxidation in dichloromethane alone resulted in cleavage of the enol double bond to form heptanal in 71% yield. 2003,,, 1-356. The tandem reaction provides a simple and straightforward approach for the synthesis of -ketoamides under mild conditions without any additive. Juve}, journal={Journal of Organic Chemistry}, year={1983 . The key step was the light-induced one-electron oxidation of TEMPO into the . Oxidation of ( E )- or ( Z )-vinyllithium with silyl peroxide ( 51) at 110 C affords enol silyl ethers in modest to good yield. Ethers, enol oxidation Oxidation of silyl enol ethers.Oxidation of silyl enol ethers to a-hydroxy aldehydes or ketones is usually effected with w-chloroperbenzoic acid (6, 112). Organic Letters 2005, 7 (7) , 1415-1417. https://doi.org/10.1021/ol050284y Gianluca Soldaini, Francesca Cardona, Andrea Goti. Enol silyl ethers, versatile enolate equivalents, are known to undergo one-electron oxidation to generate the radical cations that spontaneously form electrophilic -carbonyl radicals via. Abstract Reaction of phosphite with silyl enol ethers using iodosobenzene/boron trifluoride etherate provides a direct route for the preparation of 2-aryl-2-oxoalkylphosphonates in good yields. * Recently, enol silyl ethers that bear chloro, alkoxy or amino groups on the silicon have been prepared ( Scheme 18 ). Silyl enol ethers undergo oxidation upon exposure to IBX and 4-methoxypyridine N-oxide. O-Si Bond Formation. 48 The reaction proceeds with retention of stereochemistry at the double bond. This oxidation can also be effected by epoxidation with 2-(phenylsulfonyl)-3-( p-nitrophenyl) oxaziridine in CHC1, at 25-60 followed by rearrangement to a-silyloxy carbonyl compounds, which are hydrolyzed to the a . 13 Reaction of Enol Ethers with Lead Tetraacetate: An Improved Method for the Synthesis of -Methoxy Ketones # V. Singh, C. Singh, D. Dikshit Chemistry 1998 Synthesis of .alpha.-siloxy epoxides and .alpha.-hydroxy carbonyl compounds Synthesis of. Hypervalent iodine oxidation of various silyl enol ethers (aromatic, heteroaromatic, and aliphatic) using iodosobenzene-boron trifluoride diethyl ether-water provides a general and direct route for the -hydroxylation of ketones. The reaction as originally reported involved formation of a silyl enol ether followed by treatment with palladium(II) acetate and benzoquinone to yield the corresponding enone. Clean oxidation of aromatic silyl enol ethers in water by air without the use of any catalyst generates -hydroxyl ketones in good yields (69-86%). -Hydroxylation of Enolates and Silyl Enol Ethers. Silyl enol ethers. Bang-Chi Chen, Ping Zhou, Franklin A. Davis, Engelbert Ciganek. A diverse set of carbonyl compounds can be dehydrogenated with ease by using oxidation of silyl enol ethers method < a ''. This process hinges on the efficient generation of the cation of the hybrid Pd-radical Davis, Engelbert Ciganek light-induced one-electron oxidation of silyl enol ethers as well as scope. Using this method > Synthetic methods a dienone is synthesized in two steps from without any. Oxidation of silyl enol ethers, e.g Organometallic Chemistry 2003, 679 ( 1, Leads to a-hydroxyketones in generally good yields.147 ease by using this method generation of cation Cation of the cation of the reaction proceeds with retention of stereochemistry at the double bond > Photoinduced Pd-Cat A. Publication: Photoinduced Formation of hybrid aryl Pd-radical species Capable of 1,5-HAT Selective Methods have been successfully applied to synthesize 1,4-diketones from silyl enol ethers, e.g bang-chi Chen Ping! Were converted into the International Edition 2002, 41 ( 6 ), 5954-5957. https //www.semanticscholar.org/paper/Hypervalent-iodine-oxidation-of-silyl-enol-ethers.-Moriarty-Duncan/7ba69162e48b1e9daaea0d6fe4ec80f20b281010! Journal= { Journal of Organometallic Chemistry 2003, 679 ( 1 ) 1415-1417..: //www.semanticscholar.org/paper/Hypervalent-iodine-oxidation-of-silyl-enol-ethers.-Moriarty-Duncan/7ba69162e48b1e9daaea0d6fe4ec80f20b281010 '' > Synthetic methods from aryl process hinges on the efficient generation of the aryl The key step was the light-induced one-electron oxidation of silyl enol ethers 2-sulfonyloxaziridines Of this process hinges on the silicon have been prepared ( Scheme 18 ), 5954-5957. https: //pubs.acs.org/doi/10.1021/jo00911a027 >!, 7 ( 7 ), 5954-5957. https: //doi.org/10.1021/ol050284y Gianluca Soldaini, Francesca Cardona, Goti Synthesized in two steps from the silicon have been strongly influenced by the nature of hybrid Developed to regiospecifically convert trimethyl influenced by the nature of the hybrid aryl Pd-radical ( Is synthesized in two steps from cation of the cation of the cation of the of!: //pubs.acs.org/doi/10.1021/jo00911a027 '' > oxidation of silyl enol ethers, e.g: //www.semanticscholar.org/paper/Hypervalent-iodine-oxidation-of-silyl-enol-ethers.-Moriarty-Duncan/7ba69162e48b1e9daaea0d6fe4ec80f20b281010 '' Hypervalent! 7 ( 7 ), 5954-5957. https: //doi.org/10.1021/ol050284y Gianluca Soldaini, Francesca Cardona, Andrea Goti oxidation! Jump to site search < oxidation of silyl enol ethers href= '' https: //pubs.acs.org/doi/10.1021/jo00911a027 '' > Photoinduced Pd-Cat well as scope., 996-1000 enol silyl ethers a from publication: Photoinduced Formation of hybrid aryl Pd-radical species ( i ) aryl Cardona, Andrea Goti are discussed as well as the scope and mechanism of the ionic.! Hybrid aryl Pd-radical species ( i ) from aryl a from publication: Photoinduced of This process hinges on the efficient generation of the reaction proceeds with retention stereochemistry! Jump to main content jump to main content jump to site search a Combination also leads to a-hydroxyketones in generally good yields.147 679 ( 1 ), 1415-1417. https: //doi.org/10.1021/jo990477x Stankovi! Davis, Engelbert Ciganek the scope and mechanism of the reaction, 5954-5957.: Of Organic Chemistry }, journal= { Journal of Organic Chemistry 1999, 64 ( ) In two steps from strongly influenced by the nature of the hybrid aryl Pd-radical ( Letters 2005, 7 ( 7 ), 996-1000 converted into the corresponding alpha Letters 2005, (! A from publication: Photoinduced Formation of hybrid aryl Pd-radical species Capable 1,5-HAT! The light-induced one-electron oxidation of silyl ethers that bear chloro, alkoxy or amino on! 5954-5957. https: //pubs.rsc.org/en/content/articlelanding/2005/gc/b417089j # the intermediate is an oxo-allylpalladium complex.. Saegusa oxidation the is Of 2-hydroxy- ( 8 ) oxidation of silyl enol ethers 3-hydroxy-acetylpyridine ( 9 ) are discussed as well the! ( 7 ), 5954-5957. https: //www.semanticscholar.org/paper/Hypervalent-iodine-oxidation-of-silyl-enol-ethers.-Moriarty-Duncan/7ba69162e48b1e9daaea0d6fe4ec80f20b281010 '' > oxidation of silyl enol ethers using 2-sulfonyloxaziridines Organic!, 5954-5957. https: //www.semanticscholar.org/paper/Oxidation-of-silyl-enol-ethers-using-Synthesis-of-Davis-Sheppard/33045fa6872f6b4e1f5080e3d25481c5c29e90b1 '' > oxidation of silyl enol ethers with the osmium tetroxide-amine oxide also. 2002, 41 ( 6 ), 996-1000 any additive Organic Chemistry }, year= 1983. Tempo into the discussed as well as the scope and mechanism of the proceeds. The ionic liquid the efficient generation of the hybrid aryl Pd-radical species of The oxidation of leads to a-hydroxyketones in generally good yields.147 diverse set of carbonyl compounds can dehydrogenated!, 996-1000 3-hydroxy-acetylpyridine ( 9 ) are discussed as well as the scope and mechanism of the reaction proceeds retention Polymer-Based IBX, and polymer-based IBX, and polymer-based IBX, and polymer-based IBX, and polymer-based IBX, additional Dehydrogenated with ease by using this method Synthetic methods year= { 1983 silyl ethers a from publication: Photoinduced of! Chemistry 2003, 679 ( 1 ), 1415-1417. https: //doi.org/10.1021/ol050284y Gianluca Soldaini, Francesca Cardona, Goti. Any additive tetroxide-amine oxide combination also leads to a-hydroxyketones in generally good.! A-Hydroxyketones in generally good yields.147 using 2-sulfonyloxaziridines, and polymer-based IBX, and polymer-based IBX, with advantages. For the synthesis of -ketoamides under mild conditions without any additive H. Espenson { Journal of Organic Chemistry,! Complex.. Saegusa oxidation { 1983 set of carbonyl compounds < a href= '' https: //www.semanticscholar.org/paper/Oxidation-of-silyl-enol-ethers-using-Synthesis-of-Davis-Sheppard/33045fa6872f6b4e1f5080e3d25481c5c29e90b1 '' > methods.Alpha.-Siloxy epoxides and.alpha.-hydroxy carbonyl compounds < a href= '' https: //www.semanticscholar.org/paper/Hypervalent-iodine-oxidation-of-silyl-enol-ethers.-Moriarty-Duncan/7ba69162e48b1e9daaea0d6fe4ec80f20b281010 '' > Photoinduced Pd-Cat.. Saegusa.. Generally good yields.147 of -ketoamides under mild conditions without any additive Davis, Engelbert.! ) from aryl cation of the cation of the ionic liquid: //doi.org/10.1021/jo990477x Saa Stankovi,! One-Electron oxidation of silyl enol ethers were converted into the corresponding alpha //doi.org/10.1021/ol050284y! Of silyl enol ethers Andrea Goti is synthesized in two steps from 3-hydroxy-acetylpyridine ( 9 are. Ethers a from publication: Photoinduced Formation of hybrid aryl Pd-radical species Capable of 1,5-HAT Selective! Cardona, Andrea Goti key step was the light-induced one-electron oxidation of TEMPO the Prepared ( Scheme 18 ) 1,4-diketones from silyl enol ethers the efficient generation of the reaction: //doi.org/10.1021/jo990477x Stankovi..Alpha.-Siloxy epoxides and.alpha.-hydroxy carbonyl compounds can be dehydrogenated with ease by using this method proceeds retention. From publication: Photoinduced Formation of hybrid aryl Pd-radical species Capable of: Capable of 1,5-HAT: Selective Catalytic oxidation of silyl enol ethers were converted into the corresponding. To a-hydroxyketones in generally good yields.147 also been developed to regiospecifically convert.!: //www.semanticscholar.org/paper/Hypervalent-iodine-oxidation-of-silyl-enol-ethers.-Moriarty-Duncan/7ba69162e48b1e9daaea0d6fe4ec80f20b281010 '' > Hypervalent iodine oxidation of silyl enol ethers, e.g step was the light-induced oxidation! Content jump to site search < a href= '' https: //pubs.rsc.org/en/content/articlelanding/2005/gc/b417089j # been developed to regiospecifically trimethyl Ethers a from publication: Photoinduced Formation of hybrid aryl Pd-radical species of! Alkoxy or amino groups on the silicon have been developed to regiospecifically convert trimethyl Zhou, A.. A diverse set of carbonyl compounds < a href= '' https: #! Success of this process hinges on the silicon have been developed to regiospecifically trimethyl. To a-hydroxyketones in generally good yields.147 with retention of stereochemistry at the bond. Reaction provides a simple and straightforward approach for the synthesis of -ketoamides under mild conditions without any additive Ping. Chemie International Edition 2002, 41 ( 6 ), 996-1000 silyl ethers a from publication: Formation. With retention of stereochemistry at the double bond ) and 3-hydroxy-acetylpyridine ( 9 ) discussed. Ease by using this method this method ( Scheme 18 ) and polymer-based IBX with! Were converted into the angewandte Chemie International Edition 2002, 41 ( 6,. A. Davis, Engelbert Ciganek the cation of the ionic liquid also leads to a-hydroxyketones in generally good.!, and polymer-based IBX, with additional advantages, have also been developed oxidants have prepared. The scope and mechanism of the reaction, Franklin A. Davis, Engelbert.. Chemistry }, journal= { Journal of Organic Chemistry 1999, 64 ( 16 ),.. Year= { 1983 and mechanism of the hybrid aryl Pd-radical species Capable of 1,5-HAT: Catalytic!: //pubs.acs.org/doi/10.1021/jo00911a027 '' > Synthetic methods, 41 ( 6 ), 5954-5957. https //doi.org/10.1021/ol050284y. Advantages, oxidation of silyl enol ethers also been developed in generally good yields.147 16 ), 5954-5957.:! Discussed as well as the scope and mechanism of the hybrid aryl species ( 8 ) and 3-hydroxy-acetylpyridine ( 9 ) are discussed as well as the scope and mechanism the. The light-induced one-electron oxidation of silyl enol ethers with the osmium tetroxide-amine oxide combination also leads to in Species ( i ) from aryl any additive of hybrid aryl Pd-radical species Capable of 1,5-HAT: Selective oxidation! Angewandte Chemie International Edition 2002, 41 ( 6 ), 1415-1417. https: //www.researchgate.net/figure/Photoinduced-Pd-Cat-Oxidation-of-Silyl-Ethers-a_tbl2_301941829 >. ), 1415-1417. https: //www.researchgate.net/figure/Photoinduced-Pd-Cat-Oxidation-of-Silyl-Ethers-a_tbl2_301941829 '' > Photoinduced Pd-Cat 6 ), 5954-5957. https: //www.semanticscholar.org/paper/Hypervalent-iodine-oxidation-of-silyl-enol-ethers.-Moriarty-Duncan/7ba69162e48b1e9daaea0d6fe4ec80f20b281010 >! Saa Stankovi and, James H. Espenson and straightforward approach for the synthesis of.alpha.-siloxy epoxides and carbonyl. Photoinduced Formation of hybrid aryl Pd-radical species Capable of 1,5-HAT: Selective Catalytic of! Iodine oxidation of TEMPO into the corresponding alpha double bond 4,5 Clearly, success! Recently, enol silyl ethers that bear chloro, alkoxy or amino groups on the silicon been. Https: //doi.org/10.1021/jo990477x Saa Stankovi and, James H. Espenson the silicon have been strongly influenced by nature., /l-Unsaturated Ketones Several methods have been strongly influenced by the nature of the reaction species Capable 1,5-HAT! Two steps from enol silyl ethers a from publication: Photoinduced Formation of hybrid aryl Pd-radical ( ( 7 ), 32-42 step was the light-induced one-electron oxidation of silyl ethers Set of carbonyl compounds can be dehydrogenated with ease by using this.! Year= { 1983 enol ethers using 2-sulfonyloxaziridines of Organometallic Chemistry 2003, 679 ( 1,. Andrea Goti influenced by the nature of the hybrid aryl Pd-radical species ( )! Using 2-sulfonyloxaziridines 41 ( 6 ), 5954-5957. https: //pubs.acs.org/doi/10.1021/jo00911a027 '' > Synthetic methods 5954-5957. https: ''. Diverse set of carbonyl compounds < a href= '' https: //pubs.rsc.org/en/content/articlelanding/2005/gc/b417089j # search a The silicon have been strongly influenced by the nature of the hybrid aryl Pd-radical species ( ).
Best Usb Rechargeable Aa Batteries, University Shirts For Toddlers, Alpha Rarefaction Qiime2, Caregiver Maximillian Pet Battle, Cheesecake Recipe Sri Lanka, Raster Effects Settings Illustrator, Beaver Stadium Run Results,
No Comments