Gold(I)‐Catalyzed Alkoxyhalogenation of β‐Hydroxy‐α,α‐Difluoroynones

Abstract

Gold standard: AuCl was found to be the only suitable catalyst for the 6‐endo‐dig ring closure of hydroxylated difluorinated ynones (see scheme), a class of substrates that displays low reactivity owing to the presence of the gem‐difluoro group. For the first time, a gold catalyst is used in combination with an electrophilic fluorinating reagent.

Enantioselective Reduction of Ethyl 3‐Oxo‐5‐phenylpentanoate with Whole‐Cell Biocatalysts

“…C-C bond formation between 3-phenylpropionaldehyde and ethyl acetate afforded racemic alcohol rac-1, which was oxidized with Jones reagent (CrO 3 , H 2 SO 4 , acetone) to produce -oxo ester 2. [15,16] Scheme 1. Synthesis of ethyl 3-oxo-5-phenylpentanoate (2).…”

Gold catalyzed synthesis of fluorinated tetrahydrofurans and lactones

“…3HF as a nucleophilic fluorination reagent [14,15]. Gouverneur's group developed the first gold-catalyzed fluorination of alkyne using an electrophilic fluorination reagent (Selectfluor) [16]. Our group developed a gold catalyzed multi-component transformationfunctionalized hydration of alkynes, where various functionalized fluoroketones can be accessed in one pot [17].…”

Fluorovinyl Thioethers as Putative Steric and Electronic Thioester Enolate Mimetics: Chemoselective HF Addition to Acetylene Thioethers

“…[11] Gold-and palladium-catalysed hydrofluorination reactions of alkynes have also been recently described. [12][13][14][15][16] Fluorovinyl thioethers have been prepared by the reaction of suitable mercaptans with vinylidene fluoride in the presence of a base, [17] or via cesium fluoride-mediated cross-coupling of (1-fluorovinyl)dimethylsilane with the corresponding S-aryl benzenethiosufonate (Scheme 1). [18] Whereas the former method involves the use of a gaseous reagent under high pressure and temperature, the latter requires the preparation of both the silyl and thiosulfonate reagents for any variation of the S-aryl moiety, thus making the synthetic process rather impractical.…”