Selective Oxidation of Vinyl Ethers and Silyl Enol Ethers with Hydrogen Peroxide Catalyzed by Peroxotungstophosphate

Yamamoto, H.; Tsuda, Masaya; Sakaguchi, Satoshi; Ishii, Yasutaka

doi:10.1021/jo970440h

Cited by 35 publications

(12 citation statements)

References 43 publications

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“…With internal alkyne 22 in hand, the enyne coupling with silyl ether 6 was attempted. The expected product from this reaction was a silyl enol ether, which would then be chemoselectively oxidised to an aldehyde (eventually to be converted into the aminoethyl side chain) in the presence of the other double bond (C‐6–C‐7). In the event, treatment of 22 with silyl ether 6 resulted only in the recovery of starting material under a variety of reaction conditions.…”

Section: Resultsmentioning

confidence: 99%

A Stereoselective Synthesis of the Carbon Backbone of Phoslactomycin B

Raghavan

Patel

2017

Eur J Org Chem

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A convergent synthesis of the entire carbon framework of phoslactomycin B is disclosed. An initial route aimed to create the C‐8 tetrasubstituted stereocentre through regioselective intermolecular coupling between an internal alkyne and an allyl silyl ether, adopting Trost's protocol, followed by [2,3] sigmatropic rearrangement. But this was not successful. In a second approach, a propargylic sulfide was rearranged to give an unsaturated ketone. This was then treated with lithio acetonitrile to create the C‐8 stereocentre selectively. The C‐4 and C‐5 stereocentres were introduced by a non‐Evans syn‐aldol reaction using Crimmins's protocol. The C‐9 and C‐11 carbinol centres were created by asymmetric transfer hydrogenation. The (Z,Z)‐diene moiety was introduced by partial reduction of a diyne following Hansen's modification of the Boland reduction reaction.

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Section: Resultsmentioning

confidence: 99%

A Stereoselective Synthesis of the Carbon Backbone of Phoslactomycin B

Raghavan

Patel

2017

Eur J Org Chem

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“…[4][5][6] Thus we attempted to construct the Cu-bpy hybrid-polymer-encapsulated magnetic beads (HP-MB) in this study.…”

Section: Resultsmentioning

confidence: 99%

Organic–Inorganic Hybrid Polymer‐Encapsulated Magnetic Nanobead Catalysts

Arai

Sato

Kanoh

et al. 2008

Chemistry A European J

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A new strategy for the encapsulation of magnetic nanobeads was developed by using the in situ self-assembly of an organic-inorganic hybrid polymer. The hybrid polymer of {[Cu(bpy)(BF(4))(2)(H(2)O)(2)](bpy)}(n) (bpy=4,4'-bipyridine) was constructed on the surface of amino-functionalized magnetic beads and the resulting hybrid-polymer-encapsulated beads were utilized as catalysts for the oxidation of silyl enolates to provide the corresponding alpha-hydroxy carbonyl compounds in high yield. After the completion of the reaction, the catalyst was readily recovered by magnetic separation and the recovered catalyst could be reused several times. Because the current method did not require complicated procedures for incorporating the catalyst onto the magnetic beads, the preparation and the application of various other types of organic-inorganic hybrid-polymer-coated magnetic beads could be possible.

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“…It is well known that POMs are effective catalysts for the epoxidation of olefins in the presence of hydrogen peroxide [4][5][6][7][8][9][10][11][12]. However, their separation and recycling in the catalytic reactions is difficult due to the fact that POMs are soluble in many polar solvents.…”

Section: Introductionmentioning

confidence: 99%

Wells–Dawson heteropoly acid encapsulated into the nanocages of SBA-16 as heterogeneous catalyst for the oxidation of olefins and alcohols

et al. 2015

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Wells-Dawson type 18-tungstophosphoric acid (H 6 P 2 W 18 O 62 ) as guest was encapsulated inside the nanocages of mesoporous SBA-16 host. The pore entrance of SBA-16 material was modified by silylating reagent to prevent the escape of encapsulated H 6 P 2 W 18 O 62 from the nanocages. The prepared host-guest material was characterized by different physicochemical techniques. X-ray diffraction and transmission electron microscopy analyses indicated the retention of mesoporous structure of SBA-16 and well-dispersion of the H 6 P 2 W 18 O 62 into the nanocages of SBA-16. The obtained material exhibited high catalytic activity, stability, and recyclability in the epoxidation of olefins and oxidation of alcohols in the presence of H 2 O 2 as oxidant.

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Selective Oxidation of Vinyl Ethers and Silyl Enol Ethers with Hydrogen Peroxide Catalyzed by Peroxotungstophosphate

Cited by 35 publications

References 43 publications

A Stereoselective Synthesis of the Carbon Backbone of Phoslactomycin B

A Stereoselective Synthesis of the Carbon Backbone of Phoslactomycin B

Organic–Inorganic Hybrid Polymer‐Encapsulated Magnetic Nanobead Catalysts

Wells–Dawson heteropoly acid encapsulated into the nanocages of SBA-16 as heterogeneous catalyst for the oxidation of olefins and alcohols

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