Synthesis of Saturated Six-Membered Ring Lactones

Palanichamy, Kalanidhi; Kaliappan, Krishna P.

doi:10.1007/978-3-642-41473-2_3

Cited by 8 publications

(7 citation statements)

References 121 publications

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“…As shown with diacids 1 , 2 , 4 , and 10 , the products are transfered straightforwardly to lactones by refluxing in toluene with a stoichiometric amount of p -toluenesulfonic acid (TsOH) (Table ). Importantly, this is a new pathway to prepare aryl-substituted δ-lactone acids which are often tedious to synthesize and, therefore, rare. − …”

Section: Resultsmentioning

confidence: 99%

Synthesis of Diaryl Hydroxyl Dicarboxylic Acids from Amino Acids

et al. 2020

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Herein we report a unique method for preparing diaryl hydroxyl dicarboxylic acids in a diastereospecific manner. The three-component reaction occurs between amino acid, aromatic aldehyde, and primary alcohol in alkaline solutions under microwave-assisted conditions. The dicarboxylic acids are isolated as sodium salts in high yields (up to 77%) by direct precipitation from the reaction solution. The experimental results suggest that the diastereospecificity originates from a [3,3]-sigmatropic rearrangement followed by a sodium-assisted hydride transfer. As further shown, the previously unreported dicarboxylic acids are easily turned into corresponding δ-lactones.

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Section: Resultsmentioning

confidence: 99%

Synthesis of Diaryl Hydroxyl Dicarboxylic Acids from Amino Acids

et al. 2020

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“…After chromatographic purification, the reduction of the newly obtained oxoesters 3aa, 3ab, and 6a with NaBH 4 gave spontaneously new heterocyclic δand γ-lactones 7a,b and 8 as the major products (Scheme 4). Functionalized γand δ-lactones are valuable compounds found in a large variety of natural and synthetic biologically active substances and many efforts have been devoted to their synthesis in non-racemic form [30,31]. In particular, chiral γ-butyrolactones having an aryl group at β-stereocenter are of considerable importance in themselves and as key precursors to the synthesis of γ-aminobutyric acid derivatives [32][33][34].…”

Section: Reductive Cyclization To Heteroaryl Lactonesmentioning

confidence: 99%

Experimental and Computational Studies Unraveling the Peculiarity of Enolizable Oxoesters in the Organocatalyzed Mannich-Type Addition to Cyclic N-Acyl Iminium Ions

et al. 2020

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γ− and δ-Oxoesters are easily available starting materials that have been sparingly used in some organocatalyzed reactions proceeding with a high enantioselectivity. In our experimentation we found that the use of these compounds as the enolizable (nucleophilic) component in organocatalyzed Mannich-type reactions using in situ-generated cyclic N-acyl iminium ions gave low diastereoselectivity and low to moderate values of enantioselectivity. This significant drop of facial selectivity with respect to simple aliphatic aldehydes has been rationalized by means of density functional theory (DFT) calculations.

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“…48,49 We were also interested in exploring these conditions for a one-pot oxidative cyclization of diols into lactones. 50 Such technology would complement recent protocols for these transformations 51−71 and would increase the versatility of Selectfluor as an oxidant. What follows is an account of our efforts in these directions.…”

Section: ■ Introductionmentioning

confidence: 99%

Oxidations of Alcohols, Aldehydes, and Diols Using NaBr and Selectfluor

2023

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We present protocols for the oxidation of alcohols and aldehydes and for the oxidative cyclization of diols which use a combination of Selectfluor and NaBr. For most substrates, the optimal solvent system is a 1:1 mixture of CH3CN/H2O, but, in select cases, biphasic 1:1 mixtures of EtOAc/H2O or CH2Cl2/H2O are superior. This procedure is operationally simple, uses inexpensive and readily available reagents, and tolerates a variety of functional groups. Mechanistic studies suggest that the active oxidant is hypobromous acid, generated by the almost instantaneous oxidation of Br– by Selectfluor in an aqueous milieu.

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Synthesis of Saturated Six-Membered Ring Lactones

Cited by 8 publications

References 121 publications

Synthesis of Diaryl Hydroxyl Dicarboxylic Acids from Amino Acids

Synthesis of Diaryl Hydroxyl Dicarboxylic Acids from Amino Acids

Experimental and Computational Studies Unraveling the Peculiarity of Enolizable Oxoesters in the Organocatalyzed Mannich-Type Addition to Cyclic N-Acyl Iminium Ions

Oxidations of Alcohols, Aldehydes, and Diols Using NaBr and Selectfluor

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