@article{e8e2d34735dc4ac18eafa832e71ad9ce,
title = "Base- And Catalyst-Induced Orthogonal Site Selectivities in Acylation of Amphiphilic Diols",
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.",
author = "Natali Ashush and Reut Fallek and Amit Fallek and Roman Dobrovetsky and Moshe Portnoy",
note = "Publisher Copyright: Copyright {\textcopyright} 2020 American Chemical Society. Copyright: Copyright 2020 Elsevier B.V., All rights reserved.",
year = "2020",
month = may,
day = "15",
doi = "10.1021/acs.orglett.0c00830",
language = "אנגלית",
volume = "22",
pages = "3749--3754",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "10",
}