Synthesis of (2R, 3S)- or (2S, 3R)-2-amino-3-trifluoromethyl-3-hydroxyalkanoic acid derivatives (threonine and allo-threonine analogs) from enantiopure 4,4,4-trifluoro-3-hydroxybutanoic acid

Sting, Andrea Rolf; Seebàch, Dieter

doi:10.1016/0040-4020(95)00895-f

Cited by 41 publications

(10 citation statements)

References 47 publications

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“…1,3-Dioxan-4-ones, i.e. cyclic esters of β-hydroxyacids, were also successfully applied as substrates for these transformations [92,93]. The resulting anti isomers of N 1 ,N 2 -diprotected α-hydrazino-β-hydroxyesters, containing both hydrazinoalcohol and hydrazinoester moieties, proved to be useful starting materials for the preparation of various important compounds, e.g.…”

Section: Electrophilic Aminations Of Nucleophilic Carbons (Methods F mentioning

confidence: 98%

Chemistry of Hydrazinoalcohols and their Heterocyclic Derivatives. Part 1. Synthesis of Hydrazinoalcohols

Zalán

Lázár

Fülöp

2005

COC

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Hydrazinoalcohols are versatile di-or trifunctional compounds with wide-ranging possibilities for application in organic synthesis. Numerous methods have been devised for the preparation of this family of compounds in recent decades. This review discusses the main pathways for the synthesis of hydrazinoalcohol derivatives, including epoxide ring-openings and nucleophilic substitutions by hydrazines, addition reactions to hydroxyhydrazones, hydrazine additions to olefinic bonds, electrophilic C-and N-amination reactions, cycloadditions, reductions of N-nitroso aminoalcohols and some unique procedures. The latest developments in these fields, involving both conventional and enzymatic catalytic methods of synthetic organic chemistry, allow the highly regio-, stereo-and enantioselective preparation of hydrazinoalcohol derivatives.

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Section: Electrophilic Aminations Of Nucleophilic Carbons (Methods F mentioning

confidence: 98%

Chemistry of Hydrazinoalcohols and their Heterocyclic Derivatives. Part 1. Synthesis of Hydrazinoalcohols

Zalán

Lázár

Fülöp

2005

COC

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“…The synthesis of (2 S ,3 S )-CF 3 -threonine has been described in several publications [ 7 , 10 , 19 – 22 ]. Among these approaches, we followed a general procedure to access to (2 S ,3 S )-CF 3 -threonine through an aldol reaction of CF 3 CHO with the Ni(II) complex of the chiral Schiff base of glycine which was introduced by Belokon et al [ 23 – 24 ].…”

Section: Resultsmentioning

confidence: 99%

The use of 4,4,4-trifluorothreonine to stabilize extended peptide structures and mimic β-strands

Xu¹,

Correia²,

Ha-Duong³

et al. 2017

Beilstein J. Org. Chem.

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Pentapeptides having the sequence R-HN-Ala-Val-X-Val-Leu-OMe, where the central residue X is L-serine, L-threonine, (2S,3R)-L-CF3-threonine and (2S,3S)-L-CF3-threonine were prepared. The capacity of (2S,3S)- and (2S,3R)-CF3-threonine analogues to stabilize an extended structure when introduced in the central position of pentapeptides is demonstrated by NMR conformational studies and molecular dynamics simulations. CF3-threonine containing pentapeptides are more prone to mimic β-strands than their natural Ser and Thr pentapeptide analogues. The proof of concept that these fluorinated β-strand mimics are able to disrupt protein–protein interactions involving β-sheet structures is provided. The CF3-threonine containing pentapeptides interact with the amyloid peptide Aβ1-42 in order to reduce the protein–protein interactions mediating its aggregation process.

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“…Acidic ring-opening and removal of the N-Boc groups provided the corresponding α-hydrazino -β -hydroxyesters which, on hydrogenolysis, gave the threonine analog (2R, 3S) -2 -amino -4,4,4 -trifluoro -3-hydroxybutanoate methyl ester (1) (Figure 2). Previous synthetic and enzymatic approaches to trifluoromethyl analogs of threonine and allothreonine by other investigators are discussed in this paper (3). Enantiomerically enriched 3,3,3-trifluoroalanine (up to 63% ee) has been prepared by the asymmetric reduction of 2-(N-arylimino) -3,3,3-trifluoropropanoic acid esters with a chiral oxazaborolidine catalyst (equation 1)(4).…”

Section: Fluoroamino Acidsmentioning

confidence: 99%

Fluorine-Containing Chiral Compounds of Biomedical Interest

Filler

1999

ACS Symposium Series

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In recent years, there has been a plethora of publications on asymmetric syntheses and enzymic methods leading to fluorine-containing chiral compounds. This review, based on a detailed survey of recent literature, focuses on compounds of interest in bio-and medicinal chemistry, e.g., amino acids, anticancer agents, sugars, nucleosides, central nervous system agents, and anesthetics. Methods involving asymmetric aldol reactions, asymmetric alkylation, enantioselective fluorinating agents, and enzymically controlled reactions are presented. Bioactive fluorine-containing compounds have been known since the 1930s and 1940s, but the remarkable developments of the 1950s, including the fluorosteroids, inhalation anesthetics, such as halothane, and the anticancer agent 5-fluorouracil, heralded the subsequent rapid advances we have witnessed during the ensuing forty years.During the past decade, there has been an increased emphasis on new approaches to chiral compounds and asymmetric syntheses. This focus has been particularly pronounced in medicinal chemistry, where a specific enantiomer or diastereomer often exhibits enhanced therapeutic potency compared with the racemate. Organofluorine compounds have played a significant role in these advances. An earlier report emphasized a range of methods for the synthesis of chiral bioactive fluoroorganic compounds (1). Since the intent of this paper is to provide an overview which captures the scope and flavor of these recent developments, it seems quite appropriate to briefly cite the fascinating range of research studies of the other contributors to this book.Bravo and co-workers report asymmetric syntheses of fluoroalkylamino compounds via chiral sulfoxides and the stereoselective synthesis of β-fluoroalkyl-β-amino alcohol units using chiral sulfoxides and the Evans aldol reaction. Bégúe and colleagues discuss the stereoselective and enantioselective synthesis of trifluoromethyl amino alcohols and fluoroalkyl isoserinates. Hoffman reports the aysmmetric fluorination of α-aminoketones, while

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Synthesis of (2R, 3S)- or (2S, 3R)-2-amino-3-trifluoromethyl-3-hydroxyalkanoic acid derivatives (threonine and allo-threonine analogs) from enantiopure 4,4,4-trifluoro-3-hydroxybutanoic acid

Cited by 41 publications

References 47 publications

Chemistry of Hydrazinoalcohols and their Heterocyclic Derivatives. Part 1. Synthesis of Hydrazinoalcohols

Chemistry of Hydrazinoalcohols and their Heterocyclic Derivatives. Part 1. Synthesis of Hydrazinoalcohols

The use of 4,4,4-trifluorothreonine to stabilize extended peptide structures and mimic β-strands

Fluorine-Containing Chiral Compounds of Biomedical Interest

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