- Preparation of enantiopure butane-2,3-diacetals of glycolic acid and alkylation reactions leading to α-hydroxyacid and amide derivatives
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The preparation of butane-2,3-diacetal protected glycolic acid and related systems is described together with highly selective alkylation reactions of (R,R) and (S,S) butanediacetal protected glycolic acid. These compounds are readily deprotected to give
- Ley, Steven V.,Diez, Elena,Dixon, Darren J.,Guy, Richard T.,Michel, Patrick,Nattrass, Gillian L.,Sheppard, Tom D.
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p. 3608 - 3617
(2007/10/03)
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- Butane-2,3-diacetal-desymmetrized glycolic acid - A new building block for the stereoselective synthesis of enantiopure α-hydroxy acids
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According to a chiral memory protocol, a chiral glycolic acid equivalent, the butane-2,3-diacetal-desymmetrized glycolate 2, is obtained from chiral 3-halopropane-1,2-diols 1. Compound 2 is a new and effective building block for the synthesis of mono- and
- Diez, Elena,Dixon, Darren J.,Ley, Steven V.
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p. 2906 - 2909
(2007/10/03)
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- Synthesis of unnatural (R)-malates from L-tartrates
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The cyclic thionocarbonates of L-tartrates were cleanly converted to (R)-malates by treating with magnesium iodide or magnesium and iodine.
- Rho, Ho-Sik
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p. 843 - 847
(2007/10/03)
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- Ruthenium-catalyzed production of cyclic sulfates
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A ruthenium catalyzed method to synthesize cyclic sulfate compounds from the corresponding cyclic sulfites, and the cyclic sulfate reaction products obtained by this method. These cyclic sulfates further react with selected nucleophiles to give various substituted products. The method is an efficient means for the synthesis of chiral building blocks from tartaric acid enantiomers in high yields using an overall two-stage, one-pot reaction procedure. The chiral compounds can be transformed by nucleophilic reactions into chiral building blocks useful for the synthesis of natural biologically active products, such as antibiotics and pheromones.
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- Ruthenium-catalyzed production of cyclic sulfates
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A ruthenium catalyzed method to synthesize cyclic sulfate compounds from the corresponding cyclic sulfites, and the cyclic sulfate reaction products obtained by this method. These cyclic sulfates further react with selected nucleophiles to give various substituted products. The method is an efficient means for the synthesis of chiral building blocks from tartaric acid enantiomers in high yields using an overall two-stage, one-pot reaction procedure. The chiral compounds can be transformed by nucleophilic reactions into chiral building blocks useful for the synthesis of natural biologically active products, such as antibiotics and pheromones.
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- Cyclic sulfate compounds
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A ruthenium catalyzed method to synthesize cyclic sulfate compounds from the corresponding cyclic sulfites, and the cyclic sulfate reaction products obtained by this method. These cyclic sulfates further react with selected nucleophiles to give various su
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- A practical synthesis of D-malate esters from L-tartrate esters
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D-malate esters were synthesized in one-pot from L-tartrate esters in 70-80% overall yields via the corresponding tartrate cyclic sulfites.
- Gao,Zepp
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p. 3155 - 3158
(2007/10/02)
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- A HIGHLY EFFICIENT DEOXYDATION OF α-OXYGENATED ESTERS VIA SmI2-INDUCED ELECTRON TRANSFER PROCESS
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A variety of α-oxygenated esters, such as α-acetoxy, α-methoxy-, α-OTPH, and α-hydroxy esters were easily reduced at room temperature to give the corresponding saturated esters in good to excellent yields with the aid of an efficient electron transfer system, SmI2-THF-HMPA.The method was succesfully applied to the direct conversion of (R,R)-tartrates to (R)-malates.
- Kusuda, Kazuhiro,Junji, Inanaga,Yamaguchi, Masaru
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p. 2945 - 2948
(2007/10/02)
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- Enantioselective Syntheses of 3-Substituted 4-(Alkoxycarbonyl)-2-azetidinones from Malic Acid
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Enantioselective syntheses of 3-substituted 4-(alkoxycarbonyl)-2-azetidinones from malic acid have been developed.Alkylation of diesters of D-malic acid provided primarily the erythro products 15RS.Base-mediated inversion gave racemic threo isomers 15.Saponification of 15 and selective monoesterification provided the correspondingly substituted β-hydroxy acids 17, which could also be epimerized at the hydroxyl position.Separate conversion of the isomers 17 to the hydroxamates 18 followed by cyclization gave the desired β-lactams 19 with complete control of stereochemistry.
- Miller, Marvin J.,Bajwa, Joginder S.,Mattingly, Phillip G.,Peterson, Kathleen
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p. 4928 - 4933
(2007/10/02)
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