Synthesis and chemistry of α-iodoperfluoroacid esters

Chen, Xudong; Lemal, David M.

doi:10.1016/j.jfluchem.2006.06.003

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Cited by 3 publications

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“…NMR yields were determined using a,a,a-trifluorotoluene as an internal area standard. 13 C NMR spectra were recorded at 125.7 MHz. GC was performed on a HewlettPackard 5750 gas chromatograph, and GC/MS on a HewlettPackard 5890A gas chromatograph with a Hewlett-Packard 5971 series mass detector.…”

Section: Methodsmentioning

confidence: 99%

Functionalization of saturated fluorocarbons with and without light

Chen

Lemal

2006

Journal of Fluorine Chemistry

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Section: Methodsmentioning

confidence: 99%

Functionalization of saturated fluorocarbons with and without light

Chen

Lemal

2006

Journal of Fluorine Chemistry

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Synthesis and Chemistry of α‐Iodoperfluoroacid Esters.

Chen

Lemal

2006

ChemInform

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Direct Catalytic Asymmetric Mannich-Type Reaction of α- and β-Fluorinated Amides

et al. 2015

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The last two decades have witnessed the emergence of direct enolization protocols providing atom-economical and operationally simple methods to use enolates for stereoselective C-C bond-forming reactions, eliminating the inherent drawback of the preformation of enolates using stoichiometric amounts of reagents. In its infancy, direct enolization relied heavily on the intrinsic acidity of the latent enolates, and the reaction scope was limited to readily enolizable ketones and aldehydes. Recent advances in this field enabled the exploitation of carboxylic acid derivatives for direct enolization, offering expeditious access to synthetically versatile chiral building blocks. Despite the growing demand for enantioenriched fluorine-containing small molecules, α- and β-fluorinated carbonyl compounds have been neglected in direct enolization chemistry because of the competing and dominating defluorination pathway. Herein we present a comprehensive study on direct and highly stereoselective Mannich-type reactions of α- and β-fluorine-functionalized 7-azaindoline amides that rely on a soft Lewis acid/hard Brønsted base cooperative catalytic system to guarantee an efficient enolization while suppressing undesired defluorination. This protocol contributes to provide a series of fluorinated analogs of enantioenriched β-amino acids for medicinal chemistry.

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Synthesis and chemistry of α-iodoperfluoroacid esters

Cited by 3 publications

References 55 publications

Functionalization of saturated fluorocarbons with and without light

Functionalization of saturated fluorocarbons with and without light

Synthesis and Chemistry of α‐Iodoperfluoroacid Esters.

Direct Catalytic Asymmetric Mannich-Type Reaction of α- and β-Fluorinated Amides

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