A neighboring group participation strategy: facile synthesis of 3,5-di-O-benzoyl-2-C-methyl-d-arabino-γ-lactone

Baeyer-Villiger-Including Domino Two-Step Oxidations of β-O-Substituted Primary Alcohols: Reflection of the Migratory Aptitudes of O-Substituted Alkyl Group in the Outcome of the Reaction

“…If such a substrate undergoes the reaction in a mode similar to that of β-alkoxy alcohols, one may expect generation of 2-formyloxy-1,3-dioxolane or -dioxane products 2e-g (Scheme 6). While rare, such dialkoxymethyl carboxylates are not unprecedented [38]. However, such formates are particularly unstable and, accordingly, under the reaction conditions, their subsequent hydrolytic decomposition is possible.…”

Sulfonyl Fluorides and Their Analogs Deoxofluorination

“…Sulfuryl fluoride (SO 2 F 2 ) is a stable gas and has been widely used as a fumigant insecticide for more than 50 years [10], but it has only recently received attention as a reagent for deoxofluorination. The reaction of alcohols with SO 2 F 2 in the presence of an additional fluoride such as Et 3 NÁ3HF has been reported to be an efficient protocol for the synthesis of a wide range of alkyl fluorides [11][12][13][14]. For example, the deoxofluorination of cyclic tertiary alcohol 1 with excess SO 2 F 2 in the presence of Et 3 NÁ3HF and Et 3 N afforded the desired alkyl fluoride 2 in 87% yield (Scheme 1) [14].…”

“…The reaction of alcohols with SO 2 F 2 in the presence of an additional fluoride such as Et 3 NÁ3HF has been reported to be an efficient protocol for the synthesis of a wide range of alkyl fluorides [11][12][13][14]. For example, the deoxofluorination of cyclic tertiary alcohol 1 with excess SO 2 F 2 in the presence of Et 3 NÁ3HF and Et 3 N afforded the desired alkyl fluoride 2 in 87% yield (Scheme 1) [14]. However, further investigations are still needed to uncover the substrate scope and limitation of this deoxofluorination reaction.…”

The Synthesis of Fluorinated Carbohydrates Using Sulfuryl Fluoride as the Deoxyfluorination Reagent

“…16 However, to the best of our knowledge, only a very few examples were described of using gaseous SO 2 F 2 as a fluorination reagent directly. 14 In 2015, the Shen group 17 described one case which used SO 2 F 2 gas combined with extra fluoride additive Et 3 N•3HF to the synthesis of 3,5-di-Obenzoyl-2-deoxy-2-fluoro-2-C-methyl-D-ribono-γ-lactone. In 2017, Sanford and co-workers 18,19 reported the deoxyfluorination of phenols by the combination of SO 2 F 2 with Me 4 NF via aryl fluorosulfonate (ArOSO 2 F) intermediates.…”