Mixed organofluorine-organosilicon chemistry. 4. Perfluoroenoxysilanes: synthesis and reactivity

Doussot, Pascale; Portella, Charles

doi:10.1021/jo00076a029

Cited by 48 publications

(28 citation statements)

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“…ALQ4465, 97.0% ee, [] 20 D +52.9 (c 10, EtOH)). Characterization data of compounds 3, 4, 6, 8, 16, 29d, 30d, 34c-f, 36, and 39a- 31 and 38h 32 were prepared by the reported procedure. 27 The absolute configuration was determined by converting alcohol to the corresponding MTPA ester.…”

Section: Methodsmentioning

confidence: 99%

Asymmetric reduction of aliphatic ketones and acyl silanes using chiral anti-pentane-2,4-diol and a catalytic amount of 2,4-dinitrobenzenesulfonic acid

et al. 2010

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Abstract-Aliphatic ketones were reduced to the corresponding secondary alcohols by using anti-1,3-diol and a catalytic amount of 2,4-dinitrobenzenesulfonic acid (DNBSA) in benzene at reflux. Addition of 1-octanethiol in that media improved the efficiency of the reduction. Asymmetric reduction of aliphatic ketones was performed by using chiral anti-pentane-2,4-diol, and highly asymmetric induction (up to >99% ee) was observed in the reduction of tert-alkyl ketones. Asymmetric reduction of acyl silanes using chiral antipentane-2,4-diol and DNBSA proceeded efficiently in the absence of octanethiol and the corresponding -silyl alcohols were obtained in high yields with high ees.

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Section: Methodsmentioning

confidence: 99%

Asymmetric reduction of aliphatic ketones and acyl silanes using chiral anti-pentane-2,4-diol and a catalytic amount of 2,4-dinitrobenzenesulfonic acid

et al. 2010

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“…52 The addition of perfluoroalkyllithium reagents to aliphatic acylsilanes was fairly efficient and provided the corresponding enoxysilanes in moderate to high yields (Scheme 34). All compounds were obtained as a single stereoisomer of unknown configuration.…”

Section: Reduction/trapping Of α-Halocarbonyl Derivativesmentioning

confidence: 99%

“…163 The reaction proceeded through a first addition of the amine at C-1 with elimination of fluoride via a S N 2′ process, release of the ketone function by desilylation and finally a new addition of the amine at C-3.…”

Section: Conversion To Fluorinated Enones and Heterocyclesmentioning

confidence: 99%

Fluorinated enol ethers: their synthesis and reactivity

2015

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Thanks to the beneficial effect of fluorine substitution on the pharmacokinetic properties of molecules, an ever increasing number of marketed drugs incorporate a fluorine atom into their structure. As a consequence, the synthesis of fluorinated molecules has become a very active research field. Among the numerous approaches, fluorinated enol ethers are valuable building blocks that allow the introduction of a fluoro- or difluoromethyl group through a wide variety of reactions. The present review lists different methods for their preparation and sums up their numerous synthetic applications.

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“…The overall process for the formation of the hemiperfluoroenones 3 from perfluoroalkyl iodides and acylsilanes has been described previously 18b,20a. Depending on the experimental conditions, compounds 1 18d,20b and 2 18a can also be isolated and these two compounds are useful synthons that can be regarded as equivalents of the enones 3 (Scheme ).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Polyfluorinated Nitrogen‐Containing Heterocycles from Hemifluorinated Enones or Organofluorosilicon Building Blocks as Synthetic Equivalents

et al. 2004

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A series of polyfluorinated heterocycles has been prepared by heterocyclisation of hemifluorinated enones or organofluorosilicon synthetic equivalents with different bis(nucleophiles). These polyfluorinated building blocks were obtained by treatment of acylsilanes with perfluoro organometallic reagents. The method is general and has been applied to aliphatic, aromatic and carbohydrate derivatives, to give oxazolidines, imidazolidines, benzodia‐ and ‐thiazepines, quinolines and pyrimidines bearing both a fluorine atom and a perfluoroalkyl group in vicinal positions. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

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Mixed organofluorine-organosilicon chemistry. 4. Perfluoroenoxysilanes: synthesis and reactivity

Cited by 48 publications

References 0 publications

Asymmetric reduction of aliphatic ketones and acyl silanes using chiral anti-pentane-2,4-diol and a catalytic amount of 2,4-dinitrobenzenesulfonic acid

Asymmetric reduction of aliphatic ketones and acyl silanes using chiral anti-pentane-2,4-diol and a catalytic amount of 2,4-dinitrobenzenesulfonic acid

Fluorinated enol ethers: their synthesis and reactivity

Synthesis of Polyfluorinated Nitrogen‐Containing Heterocycles from Hemifluorinated Enones or Organofluorosilicon Building Blocks as Synthetic Equivalents

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