Asymmetric synthesis of fluorine-containing amines, amino alcohols, α- and β-amino acids mediated by chiral sulfinyl group

Sorochinsky, Alexander E.; Soloshonok, Vadim A.

doi:10.1016/j.jfluchem.2009.09.015

Cited by 148 publications

(38 citation statements)

References 127 publications

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“…Upon treatment with typical agents, the sulfinyl auxiliary was removed and diverse derivatives of the amino trifluoromethyl alcohols 45-47 were obtained. Analogous conversions with higher substituted sulfinylmethyl residues (CHMe, CHPr, CHPh instead of CH 2 ) were reported by the same research group [43] and reviewed in a recent survey [44]. In addition to conversions presented in Scheme 19, (S,S,R)-48 yielded, after heating in boiling xylene, the optically active vinyl-substituted amino alcohol (S)-49 in 82% yield [43] (Scheme 20).…”

Section: Ring Opening Of Trifluoromethyloxiranes With N-nucleophilesmentioning

confidence: 74%

Synthesis of β-amino-α-trifluoromethyl alcohols and their applications in organic synthesis

Mlostoń

Obijalska

Heimgartner

2010

Journal of Fluorine Chemistry

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A comprehensive overview on methods applied for syntheses of β-amino-α-trifluoromethyl alcohols, including stereocontrolled variants, is presented. In addition, reported cases of the exploration of β-amino-α-trifluoromethyl alcohols for the preparation of trifluoromethylated peptidomimetics and other biologically active, fluorinated compounds are discussed. Attractive opportunities for their applications as organocatalysts are also presented.

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Section: Ring Opening Of Trifluoromethyloxiranes With N-nucleophilesmentioning

confidence: 74%

Synthesis of β-amino-α-trifluoromethyl alcohols and their applications in organic synthesis

Mlostoń

Obijalska

Heimgartner

2010

Journal of Fluorine Chemistry

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“…First of all they are recognized as valuable and efficient reagents in synthetic chemistry, particularly for asymmetric synthesis due to high asymmetric induction exerted by a sulfinyl fragment, and its configurational stability. 69,71,[74][75][76] Several review articles are devoted to this topic. [77][78][79][80][81][82][83][84] Moreover, sulfoxides are present in many natural products and they play an important role in biology.…”

Section: The Sde Of Chiral Sulfoxides During Their Gravity-driven Silmentioning

confidence: 99%

Self-disproportionation of enantiomers (SDE) of chiral sulfur-containing compounds via achiral chromatography

Drabowicz¹,

Koprowski²,

Wzorek³

et al. 2017

Arkivoc

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This review presents a comprehensive, critical treatment of all the literature data related to the phenomenon of the SDE taking place during gravity-driven achiral chromatography of scalemic compounds bearing sulfoxide and thioamide functionalities. The discussion is focused on the SDE magnitude as a function of the structure iof the compound, composition of eluent and stationary phase, including some mechanistic details. An apparent possibility of application of the SDE phenomenon via achiral chromatography as a novel, emerging unconventional enantiomeric purification technique is also discussed.

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“…Introduction of Ar-C-F group in compound 8 a (Scheme 2) led to blue shift of l max due to the high electron-withdrawing effect of Ar-C-F group. 17,18,[27][28][29] ii. IR absorption spectrum of compound 2 a showed presence of polyfunctional groups at n 3529 (OH) confirmed from their 13 CNMR data.…”

Section: Spectroscopic Characterizationmentioning

confidence: 99%

“…26 The introduction of fluorine atoms to bioactive molecules often improve their pharmacological properties because the increased permeability and hydrophobic binding and stability against metabolic transformations. 27,29 In view of the biocidal activity of fluorine atoms to bioactive molecules, great attention has been oriented in this study towards synthesis of new fluorinated 5-arylidene-4-oxo-(sulfonamoyl phenyl)-spiro [thiazolidino-2, 2¢-steroids]; 3-sulfonamoylphenyl-spiro [4-oxo-thiazolidin-2,2¢steroids] and 4-fluoroarylidene derivatives. Thus, the present study is focused on: i) synthesis and characterization of new spirothiazolidinone steroids bearing sulfa drug moieties and the corresponding 4-fluoroarylidene derivatives; ii) studying the biocidal and voltammetric behavior of selected spirothiazolidinone-steroid derivatives and finally iii) immobilization of one of the steroid reagent onto polyurethane foam sorbent as solid phase sorbent for preconcentration of bismuth (III) ions from aqueous media.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Voltammetric and Analytical Applications of Some Fluorine Substituted Spirosteroidalthiazolidin‐4‐one Derivatives of Sulfa Drugs

Makki

Al-Footy

Abdel‐Rahman

et al. 2016

J Chinese Chemical Soc

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A new 5-arylidene-4-oxo-(sulfonamoyl phenyl)-spiro[thiazolidinone-2, 2¢-steroids] series (7-10) was prepared by condensation of sulfanilamide, sulfapyridine and sulfadiazine sulfa drugs with testosterone, epiandrosterone and progesterone steroids, respectively. The resultant imino derivatives 1-3 upon cycloaddition with thioacetic acid in dry 1,4-dioxane afforded 3-sulfo-namoylphenylspiro[4-oxothiazolidin-2, 2¢steroids] (4-6). The latter compounds (4-6) upon condensation with p-fluorobenzaldehyde in ethanol-piperidine yielded the corresponding 4-fluoroarylidene derivatives 7, 8 & 9, respectively. All the newly synthesized compounds were confirmed by UV, IR, 1 H NMR, 13 C NMR, mass spectral data, elemental analysis and molecular weight determination. In vitro antimicrobial screening of some of the synthesized compounds showed good antimicrobial activities towards some pathogenic Gram-positive, Gram-negative bacteria and fungi vs. piperacillin and mycostatine antibiotics as standard antibacterial and antifungal agents, respectively. The voltammetric behavior of two newly spirothiazolidinone steroids (2a & 5a) was critically studied. Compound 5a physically immobilized polyurethane foam solid sorbent was successfully used for removal and/or separation of bismuth(III) from water.

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Asymmetric synthesis of fluorine-containing amines, amino alcohols, α- and β-amino acids mediated by chiral sulfinyl group

Cited by 148 publications

References 127 publications

Synthesis of β-amino-α-trifluoromethyl alcohols and their applications in organic synthesis

Synthesis of β-amino-α-trifluoromethyl alcohols and their applications in organic synthesis

Self-disproportionation of enantiomers (SDE) of chiral sulfur-containing compounds via achiral chromatography

Synthesis, Voltammetric and Analytical Applications of Some Fluorine Substituted Spirosteroidalthiazolidin‐4‐one Derivatives of Sulfa Drugs

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