Phosphorylation Organocatalysts Highly Active by Design

Amit Fallek, Mor Weiss-Shtofman, Maria Kramer, Roman Dobrovetsky*, Moshe Portnoy

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

The activity of nucleophilic organocatalysts for alcohol/phenol phosphorylation was enhanced through attaching oligoether appendages to a benzyl substituent on imidazole- or aminopyridine-based active units, presumably because of stabilizing n-cation interactions of the ethereal oxygens with the positively charged aza-heterocycle in the catalytic intermediates, and was substantially higher than that of known benchmark catalysts for a range of substrates. Density functional theory calculations and the study of analogues having a lower potential for such stabilizing interactions support our hypothesis.

Original languageEnglish
Pages (from-to)3722-3727
Number of pages6
JournalOrganic Letters
Volume22
Issue number9
DOIs
StatePublished - 1 May 2020

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