Synthesis of amino-methylene-gem-bisphosphonates containing an aziridine motif: Studies of the reaction scope and insight into the mechanism - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Journal of Organic Chemistry Année : 2021

Synthesis of amino-methylene-gem-bisphosphonates containing an aziridine motif: Studies of the reaction scope and insight into the mechanism

Résumé

A broad range of N-carbamoyl aziridines were obtained and then treated by the diethyl phosphonate anion to afford α-methylene-gem-bisphosphonate aziridines. Study of the reaction's scope and additional experiments indicate that the transformation proceed via a new mechanism involving the chelation of lithium ion. This last is crucial for the reaction to occur and disfavors the aziridine ringopening. A phosphonate-phosphate rearrangement from a -hydroxybisphosphonate aziridine intermediate is also proposed for the first time. This reaction provides a simple and convenient method for the synthesis of highly functionalized phosphonylated aziridine motif.
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Dates et versions

hal-03407451 , version 1 (28-10-2021)

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Suzanne Peyrottes, Thomas Cheviet. Synthesis of amino-methylene-gem-bisphosphonates containing an aziridine motif: Studies of the reaction scope and insight into the mechanism. Journal of Organic Chemistry, 2021, 86 (4), pp.3107-3119. ⟨10.1021/acs.joc.0c02434⟩. ⟨hal-03407451⟩
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