1,3-Dioxan-5-ones: synthesis, deprotonation, and reactions of their lithium enolates
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A general synthetic route to 2-alkyl and 2,2-dialkyl-1,3-dioxan-5-ones, using tris(hydroxymethyl)-nitromethane as the starting material, is described in this article.Abstract:
A general synthetic route to 2-alkyl- and 2,2-dialkyl-1,3-dioxan-5-ones, using tris(hydroxymethyl)-nitromethane as the starting material, is described. Deprotonation of these compounds was studied....read more
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The Dihydroxyacetone Unit—A Versatile C3 Building Block in Organic Synthesis
TL;DR: The related 1,3-dioxins are useful equivalents of 2-substituted acrolein derivatives that deserve particular attention, as their applicability in organic synthesis is not limited to (stereoselective) aldol reactions.
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Catalytic Enantioselective Alkylation of Substituted Dioxanone Enol Ethers: Ready Access to C(α)-Tetrasubstituted Hydroxyketones, Acids, and Esters
TL;DR: Palladium-catalyzed asymmetric alkylation enables access to fully substituted enantioenriched oxygenated stereocenters, which can be transformed easily to α-hydroxyketones, esters, and acids, providing a catalytic, enantioselective synthesis for natural products.
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Anti-selective glycolate aldol additions with an oxapyrone boron enolate.
TL;DR: The boron enolate of pyrone 2 undergoes asymmetric aldol reactions with aldehydes to give protected anti 1,2-diols 3 to give differentially protected diol intermediates 12 that are amenable to multistep synthesis.
References
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Rapid chromatographic technique for preparative separations with moderate resolution
Abstract: (11) Potassium ferricyanide has previously been used to convert w'c-1,2-dicarboxylate groups to double bonds. See, for example, L. F. Fieser and M. J. Haddadln, J. Am. Chem. Soc., 86, 2392 (1964). The oxidative dldecarboxylation of 1,2-dlcarboxyllc acids is, of course, a well-known process. See Inter alia (a) C. A. Grob, M. Ohta, and A. Weiss, Helv. Chim. Acta, 41, 1911 (1958); and (b) E. N. Cain, R. Vukov, and S. Masamune, J. Chem. Soc. D, 98 (1969).
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Advanced organic chemistry
TL;DR: In this paper, advanced organic chemistry, Advanced organic chemistry (AOC), Advanced organic Chemistry (ACC), Advanced Organic Chemistry (AOG), Advanced OCL, Advanced OCC (ACO),
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Highly selective, kinetically controlled enolate formation using lithium dialkylamides in the presence of trimethylchlorosilane
E. J. Corey,Andrew W. Gross +1 more
TL;DR: In this paper, a deprotonation of ketones and esters with lithium dialkylamides in the presence of trimethylchlorosilane leads to enhanced selectivity for the kinetically generated enolate.
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Solution structures of lithium dialkylamides and related N-lithiated species: results from lithium-6-nitrogen-15 double labeling experiments
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Enantioselective deprotonation by chiral lithium amide bases: asymmetric synthesis of trimethylsilyl enol ethers from 4-alkylcyclohexanones.
TL;DR: This work states that high-field magnetization measurements were made a t the Francis Bitter National Magnet Laboratory, which is supported at M.B.T by the National Science Foundation.