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Macrolactonization Reactions Driven by a Pentafluorobenzoyl Group **
Author(s) -
Force Guillaume,
Perfetto Anna,
Mayer Robert J.,
Ciofini Ilaria,
Lebœuf David
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202105882
Subject(s) - reactivity (psychology) , chemistry , combinatorial chemistry , group (periodic table) , computation , computational chemistry , organic chemistry , computer science , algorithm , medicine , alternative medicine , pathology
Macrolactones constitute a privileged class of natural and synthetic products with a broad range of applications in the fine chemicals and pharmaceutical industry. Despite all the progress made towards their synthesis, notably from seco ‐acids, a macrolactonization promoter system that is effective, selective, flexible, readily available, and, insofar as possible, compatible with manifold functional groups is still lacking. Herein, we describe a strategy that relies on the formation of a mixed anhydride incorporating a pentafluorophenyl group which, due to its high electronic activation enables a convenient access to macrolactones, macrodiolides and esters with a broad versatility. Kinetic studies and DFT computations were performed to rationalize the reactivity of the pentafluorophenyl group in macrolactonization reactions.