A simple and highly diastereoselective preparation of glycal epoxides using the MCPBA-KF complex

Bellucci, Giuseppe; Catelani, Giorgio; Chiappe, Cinzia; D’Andrea, Felicia

doi:10.1016/s0040-4039(00)74426-1

Cited by 52 publications

(27 citation statements)

References 14 publications

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“…However, the instability and explosivity of DMDO are serious drawbacks. Other proposed methods include m-chloroperbenzoic acid/KF [7] and Tf 2 O with diphenyl sulfoxide. [8] These methods all use stoichiometric amounts of reagents, resulting in large amounts of waste.…”

Section: Introductionmentioning

confidence: 99%

Tandem Epoxidation‐Alcoholysis or Epoxidation‐Hydrolysis of Glycals Catalyzed by Titanium(IV) Isopropoxide or Venturello’s Phosphotungstate Complex

et al. 2008

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Venturello’s phosphotungstate complex and titanium(IV) isopropoxide [Ti(O‐i‐Pr)4] were successfully used as catalysts for the epoxidation‐alcoholysis of glycals using hydrogen peroxide [H2O2]. Reaction substrates included a range of variously protected glycals and different alcohols were used as solvents. Ti(O‐i‐Pr)4 was only effective in methanol as solvent, but gave methyl glycosides in high yields and high selectivities. The Venturello complex proved to be a very versatile and efficient catalyst. Apart from epoxidation‐alcoholysis in alcoholic solvents it also showed activity in biphasic conditions to allow for glycosylation of long‐chain alcohols and was very effective in the stereoselective dihydroxylation of benzylated glucal.

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Section: Introductionmentioning

confidence: 99%

Tandem Epoxidation‐Alcoholysis or Epoxidation‐Hydrolysis of Glycals Catalyzed by Titanium(IV) Isopropoxide or Venturello’s Phosphotungstate Complex

et al. 2008

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“…Epoxidation accompanied by concomitant stereo-and regioselective opening of the epoxide is a useful method to functionalize the double bond in glucals. [22][23][24][25][26][27][28] Thus, reaction of 9 with m-CPBA in methanol in the presence of NaHCO 3 led to the stereoselective formation of 10 in 60% yield. Methylation of the newly created alcohol with MeI and Ag 2 O 29 cleanly alkylated the secondary hydroxyl group.…”

Section: Resultsmentioning

confidence: 98%

An expedient synthesis of d-callipeltose

Pihko

Nicolaou

Koskinen

2001

Tetrahedron: Asymmetry

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“…On comparison with the alternative epoxidation methods of glycals based on DMDO [2] or MCPBA/KF, [4] the MTO/UHP procedure showed a lower level of stereoselectivity, except in the oxidation of darabinal derivatives. However, we have shown that the stereoselectivity in the MTO-catalyzed epoxidation of glycals is strongly affected by the solvent used and the presence of donor additives.…”

Section: Full Papersmentioning

confidence: 97%

“…Therefore, its replacement with safer and more stable oxidants, particularly for large-scale preparations, is a valuable task. Other reagents have been proposed to perform the epoxidation, namely methyl(trifluoromethyl)dioxirane, [3] MCPBA/KF, [4] or perfluoro-cis-2,3-dialkyloxaziridines, [5] always as stoichiometric oxidants, but have never entered into practical use. No general catalytic oxidation procedure had been reported for this type of transformation until our recent disclosure of a domino oxidation-nucleophilic addition catalyzed by methyltrioxorhenium.…”

Section: Introductionmentioning

confidence: 99%

Methyltrioxorhenium‐Catalyzed Epoxidation‐Methanolysis of Glycals under Homogeneous and Heterogeneous Conditions

et al. 2006

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Abstract:The efficient and high yielding domino epoxidation-methanolysis of glycals 8 -15 has been achieved by oxidation with UHP in MeOH catalyzed by MTO. The products have been conveniently isolated as 2-acetoxy derivatives 16 -23a, b by direct acetylation of the crude mixtures. Homogeneous MTOamine complexes 5 -7, heterogeneous poly(4-vinylpyridine)/MTO compounds I -III, and microencapsulated polystyrene/MTO systems IV -VII were also tested and demonstrated their effectiveness as catalysts for the oxidation step. The facial diastereoselectivity of the oxidation ranged from satisfactory to excellent depending on the substrate and could be optimized by ample screening of catalysts. Complete conversions of substrates and nearly quantitative yields of products were obtained under environmentally friendly experimental conditions and with the use of simple work-up procedures.

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A simple and highly diastereoselective preparation of glycal epoxides using the MCPBA-KF complex

Cited by 52 publications

References 14 publications

Tandem Epoxidation‐Alcoholysis or Epoxidation‐Hydrolysis of Glycals Catalyzed by Titanium(IV) Isopropoxide or Venturello’s Phosphotungstate Complex

Tandem Epoxidation‐Alcoholysis or Epoxidation‐Hydrolysis of Glycals Catalyzed by Titanium(IV) Isopropoxide or Venturello’s Phosphotungstate Complex

An expedient synthesis of d-callipeltose

Methyltrioxorhenium‐Catalyzed Epoxidation‐Methanolysis of Glycals under Homogeneous and Heterogeneous Conditions

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