Base- And Catalyst-Induced Orthogonal Site Selectivities in Acylation of Amphiphilic Diols

Natali Ashush, Reut Fallek, Amit Fallek, Roman Dobrovetsky, Moshe Portnoy

Research output: Contribution to journalArticlepeer-review

Abstract

Seeking to selectively functionalize natural and synthetic amphiphiles, we explored acylation of model amphiphilic diols. The use of a nucleophilic catalyst enabled a remarkable shift of the site selectivity from the polar site, preferred in background noncatalyzed or base-promoted reactions, to the apolar site. This tendency was significantly enhanced for organocatalysts comprising an imidazole active site surrounded by long/branched tails. An explanation of these orthogonal modes of selectivity is supported by competitive experiments with monoalcohol substrates.

Original languageEnglish
Pages (from-to)3749-3754
Number of pages6
JournalOrganic Letters
Volume22
Issue number10
DOIs
StatePublished - 15 May 2020

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