Allyl ethyl carbonate/palladium (0), a new system for the one step conversion of alcohols into allyl ethers under neutral conditions

Lakhmiri, Rajae; Lhoste, Paul; Sinou, Denis

doi:10.1016/s0040-4039(01)80770-x

Cited by 82 publications

(21 citation statements)

References 10 publications

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“…Nucleophilic substances are alkylated by DMC with CO 2 elimination. These substances include phenols, thiols [9], [540][541][542][543][544][545][546][547][548], amines [8], [549], [550], amides and urethanes [551], [552], alcohols [553][554][555], even if these contain trialkylamino groups (i.e., usually, under similar conditions, the trialkylamino groups are quaternized and/or split off, but not in this case) [556], [557], and carboxylic acids and their anhydrides [558][559][560][561][562]. In all cases, the corresponding carbonates are produced, often as isolable intermediates, which split off CO 2 under more extreme conditions.…”

Section: Use For Chemical Synthesismentioning

confidence: 99%

Carbonic Esters

Buysch

2000

Ullmann's Encyclopedia of Industrial Chemistry

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The article contains sections titled: 1. Introduction 2. Properties 3. Production 3.1. Phosgenation of Alcohols 3.2. Phosgenation of Phenols 3.3. Oxidative Carbonylation of Alcohols 3.4. Oxidative Carbonylation of Phenols 3.5. Oxidative Carbonylation of Alcohols with NO x 3.6. Carbonic Esters from Oxalic Esters 3.7. Electrochemical Oxidative Carbonylation of Alcohols 3.8. Reaction of CO 2 with Oxiranes 3.9. Reactions of Alcohols with Urea 3.10. Reaction of Phenols with Urea 3.11. Miscellaneous Reactions of CO 2 to Form Carbonates 3.12. Transesterification 3.13. Cyclic Carbonic Esters 4. Environmental Protection and Toxicology 5. Quality Specifications 6. Analysis 7. Storage and Transportation 8. Uses 8.1. Direct Uses 8.2. Use for Chemical Synthesis 9. Economic Aspects

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Section: Use For Chemical Synthesismentioning

confidence: 99%

Carbonic Esters

Buysch

2000

Ullmann's Encyclopedia of Industrial Chemistry

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“…[37] One important result of this work is that the allylation of anomeric hydroxy groups is much more facile, which has been attributed to their higher acidity. More recently, Haight et al discovered, for primary, secondary and tertiary alcohols bearing no further functional groups, that the leaving group of the allyl carbonate exerts a strong influence on the efficiency of the reaction.…”

Section: Resultsmentioning

confidence: 95%

Palladium‐Catalyzed O‐Allylation of α‐Hydroxy Carbonyl Compounds

Schmidt

Nave

2006

Adv Synth Catal

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“…Attempted p-methoxybenzylation or allylation of 11 and 12 under mild acidic conditions [24] and p-methoxybenzylation with p-methoxybenzyl trichloroacetimidate [25] did not give satisfactory results. Allylation of 11 and 12 with methyl allylcarbonate/Pd [26] afforded the rearranged 1-O-allyl derivatives 13 and 14, respectively. However, methoxymethylation in the presence of iPr 2 EtN [17] afforded the 2-O-methoxymethyl derivatives 15 and 16 in good yields.…”

Section: Resultsmentioning

confidence: 99%

Phospholipase Cleavage of D‐ and L‐chiro‐Glycosylphosphoinositides Asymmetrically Incorporated into Liposomal Membranes

Bonilla

Cid

Contreras

et al. 2006

Chemistry A European J

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The nature of chiro-inositol-containing inositolphosphoglycans (IPGs), reported to be putative insulin mediators, was studied by examination of the substrate specificities of the phosphatidylinositol-specific phospholipase C (PI-PLC) and the glycosylphosphatidylinositol-specific phospholipase D (GPI-PLD) by using a series of synthetic D- and L-chiro-glycosylphosphoinositides. 3-O-alpha-D-Glucosaminyl- (3) and -galactosaminyl-2-phosphatidyl-L-chiro-inositol (4), which show the maximum stereochemical similarity to the 6-O-alpha-D-glucosaminylphosphatidylinositol pseudodisaccharide motifs of GPI anchors, were synthesized and asymmetrically incorporated into phospholipid bilayers in the form of large unilamellar vesicles (LUVs). Similarly, 2-O-alpha-D-glucosaminyl- (5) and -galactosaminyl-1-phosphatidyl-D-chiro-inositol (6), which differ from the corresponding pseudodisaccharide motif of the GPI anchors only in the axial orientation of the phosphatidyl moiety, were also synthesized and asymmetrically inserted into LUVs. The cleavage of these synthetic molecules in the liposomal constructs by PI-PLC from Bacillus cereus and by GPI-PLD from bovine serum was studied with the use of 6-O-alpha-D-glucosaminylphosphatidylinositol (7) and the conserved GPI anchor structure (8) as positive controls. Although PI-PLC cleaved 3 and 4 with about the same efficiency as 7 and 8, this enzyme did not accept 5 or 6. GPI-PLD accepted both the L-chiro- (3 and 4) and the D-chiro- (5 and 6) glycosylinositolphosphoinositides. Therefore, IPGs containing L-chiro-inositol only are expected to be released from chiro-inositol-containing GPIs if the cleavage is effected by a PI-PLC, whereas GPI-PLD cleavage could result in both L-chiro- and D-chiro-inositol-containing IPGs.

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Allyl ethyl carbonate/palladium (0), a new system for the one step conversion of alcohols into allyl ethers under neutral conditions

Cited by 82 publications

References 10 publications

Carbonic Esters

Carbonic Esters

Palladium‐Catalyzed O‐Allylation of α‐Hydroxy Carbonyl Compounds

Phospholipase Cleavage of D‐ and L‐chiro‐Glycosylphosphoinositides Asymmetrically Incorporated into Liposomal Membranes

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