Improving Site Selectivity in Phosphorylation of Amphiphilic Diols through Catalyst Design

Amit Fallek, Or Fleischer, Fatma Saady, Moshe Portnoy*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

Organocatalysts based on a nucleophilic core, decorated with long hydrocarbon or oligoether outer-sphere tails were successfully applied for attenuating the site selectivity in phosphorylation of a model amphiphilic diol. Under the influence of the catalysts, the preference for the first functionalization of the hydroxyl at the apolar domain increased dramatically to render the ratio up to 3.9 : 1 between the monophosphorylated products, at 50 % substrate consumption (vs. 1.8 : 1 in the alike reaction without the catalyst). A considerable influence of the catalyst design, particularly the core nature and the tails structure, on the rate and the selectivity of the reaction was observed.

Original languageEnglish
Article numbere202201089
JournalEuropean Journal of Organic Chemistry
Volume2022
Issue number46
DOIs
StatePublished - 12 Dec 2022

Funding

FundersFunder number
United States - Israel Binational Science Foundation
United States-Israel Binational Science Foundation

    Keywords

    • Alcohols
    • Amphiphiles
    • Organocatalysis
    • Phosphorylation
    • Site selectivity

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