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Asymmetric Synthesis of Bioactive Fluorinated Sulfonyl-Cyclobutene Derivatives via P(III)/P(V) Redox Catalysis
Mathieu Zimmermann1, Pascal Retailleau1, Arnaud Voituriez1
1Université Paris-Saclay, CNRS, UPR 2301, Institut de Chimie des Substances Naturelles, Gif-sur-Yvette 91198, France.
Abstract:
An efficient tandem Michael addition/intramolecular Wittig olefination has been developed for the enantioselective synthesis of fluorinated sulfonyl cyclobutenes. The reactions were performed in the presence of a catalytic amount of a chiral phosphine and phenylsilane to in situ reduce the corresponding phosphine oxide, leading to a variety of functionalized cyclobutenes isolated with up to 90% ee. After different postfunctionalizations, preliminary biological evaluations of these new molecules of interest revealed significant cytotoxicity against leukemia K562 cells.
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