Asymmetric synthesis of 2-alkyl-substituted 2-hydroxyglutaric acid γ-lactones

Paju, Anne; Laos, Marit; Jõgi, Artur; Päri, M.; Jäälaid, Raissa; Pehk, Tõnis; Kanger, Tõnis; Lopp, Margus

doi:10.1016/j.tetlet.2006.04.013

Cited by 16 publications

(4 citation statements)

References 17 publications

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“…The asymmetric oxidation of 3-substituted cyclopentane-1,2-diones 87a – f is an efficient tool in organic synthesis for the preparation of unsymmetrical γ-lactone acids 88a – f with high optical purity and good yields ( Table 6 ). These γ-lactone acids are valuable substrates for the synthesis of compounds with potentially useful pharmacological properties, such as homocitrates, alkyl- and aryl-substituted nucleosides [ 270 – 272 ].…”

Section: Reviewmentioning

confidence: 99%

Rearrangements of organic peroxides and related processes

Yaremenko¹,

Vil²,

Demchuk³

et al. 2016

Beilstein J. Org. Chem.

194

136

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SummaryThis review is the first to collate and summarize main data on named and unnamed rearrangement reactions of peroxides. It should be noted, that in the chemistry of peroxides two types of processes are considered under the term rearrangements. These are conventional rearrangements occurring with the retention of the molecular weight and transformations of one of the peroxide moieties after O–O-bond cleavage. Detailed information about the Baeyer−Villiger, Criegee, Hock, Kornblum−DeLaMare, Dakin, Elbs, Schenck, Smith, Wieland, and Story reactions is given. Unnamed rearrangements of organic peroxides and related processes are also analyzed. The rearrangements and related processes of important natural and synthetic peroxides are discussed separately.

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Section: Reviewmentioning

confidence: 99%

Rearrangements of organic peroxides and related processes

Yaremenko¹,

Vil²,

Demchuk³

et al. 2016

Beilstein J. Org. Chem.

194

136

View full text Add to dashboard Cite

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“…Subsequent transformation of adduct 30 into the thiolactone 31 , as well as adduct 33 into the lactone derivative 34 , by simple ring opening under mild acid and/or basic conditions, illustrates the utility of the method. In addition, formation of known lactone 35 from 34 served to establish the stereochemical course of the reactions. It should also be noted that both 25a and 26a upon treatment with either methyl acrylate or tert -butyl acrylate under the above conditions did not provided the corresponding Michael adducts.…”

Section: Resultsmentioning

confidence: 99%

Enantioselective Construction of Tetrasubstituted Stereogenic Carbons through Brønsted Base Catalyzed Michael Reactions: α′-Hydroxy Enones as Key Enoate Equivalent

et al. 2014

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Catalytic and asymmetric Michael reactions constitute very powerful tools for the construction of new C-C bonds in synthesis, but most of the reports claiming high selectivity are limited to some specific combinations of nucleophile/electrophile compound types, and only few successful methods deal with the generation of all-carbon quaternary stereocenters. A contribution to solve this gap is presented here based on chiral bifunctional Brønsted base (BB) catalysis and the use of α'-oxy enones as enabling Michael acceptors with ambivalent H-bond acceptor/donor character, a yet unreported design element for bidentate enoate equivalents. It is found that the Michael addition of a range of enolizable carbonyl compounds that have previously demonstrated challenging (i.e., α-substituted 2-oxindoles, cyanoesters, oxazolones, thiazolones, and azlactones) to α'-oxy enones can afford the corresponding tetrasubstituted carbon stereocenters in high diastereo- and enantioselectivity in the presence of standard BB catalysts. Experiments show that the α'-oxy ketone moiety plays a key role in the above realizations, as parallel reactions under identical conditions but using the parent α,β-unsaturated ketones or esters instead proceed sluggish and/or with poor stereoselectivity. A series of trivial chemical manipulations of the ketol moiety in adducts can produce the corresponding carboxy, aldehyde, and ketone compounds under very mild conditions, giving access to a variety of enantioenriched densely functionalized building blocks containing a fully substituted carbon stereocenter. A computational investigation to rationalize the mode of substrate activation and the reaction stereochemistry is also provided, and the proposed models are compared with related systems in the literature.

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“…The signal for C-5 in the lactone of each diastereomers resonated at  = 85.5 and 85.9 ppm. 22 Additionally, this lactone was further characterized using IR and MS spectroscopy. In the IR spectrum of 14, absorption at 1774 cm -1 indicated the presence of the lactone carbonyl functional group, and the broad absorption from 2913-3538 cm -1 was indicative of the hydroxyl group of the carboxylic acid.…”

Section: Letter Synlettmentioning

confidence: 99%

Synthesis and Biological Activity of 2-(2-Amino-2-phenylethyl)-5-oxotetrahydrofuran-2-carboxylic Acid: A Microwave-Assisted 1,3-Dipolar Cycloaddition Approach

Urquilla

Merrer

Sumner

et al. 2021

Synlett

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The microwave-assisted 1,3-dipolar cycloaddition of furanyl and benzyl oximes, and several methyl acrylates effectively provided several isoxazoline when mediated by diacetoxyiodobenzene. The selected isoxazoline, methyl-5-(3-methoxy-3-oxopropyl)-3-phenyl-4,5-dihydro isoxazole-5-carboxylate was rapidly transformed to the γ-lactone carboxylic acid, 2-(2-Amino-2-Phenylethyl)-5-Oxotetrahydrofuran-2-carboxylic acid in reasonable yield. The biological activity of this γ-lactone carboxylic acid revealed an increase in the growth of E. coli organisms by about 44% and has potential significance in stem cell research.

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Asymmetric synthesis of 2-alkyl-substituted 2-hydroxyglutaric acid γ-lactones

Cited by 16 publications

References 17 publications

Rearrangements of organic peroxides and related processes

Rearrangements of organic peroxides and related processes

Enantioselective Construction of Tetrasubstituted Stereogenic Carbons through Brønsted Base Catalyzed Michael Reactions: α′-Hydroxy Enones as Key Enoate Equivalent

Synthesis and Biological Activity of 2-(2-Amino-2-phenylethyl)-5-oxotetrahydrofuran-2-carboxylic Acid: A Microwave-Assisted 1,3-Dipolar Cycloaddition Approach

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