Umpolung Reactivity of in Situ Generated Phosphido-Boranes: An Entry to P-Stereogenic Aminophosphine-Boranes

Sébastien Lemouzy (1) , Romain Membrat (1) , Enzo Olivieri (1) , Marion Jean (1) , Muriel Albalat (1) , Didier Nuel (1) , Laurent Giordano (1) , Damien Hérault (1) , Gérard Buono (1)

1 ISM2 - Institut des Sciences Moléculaires de Marseille

The synthesis of P-stereogenic aminophos-phine-boranes has been developed on the basis of umpolung reactivity of in situ generated alkylarylphosphido-boranes, which are normally configurationally unstable intermediates. In our case, their high configurational stability was due to the slow release of the hydroxyalkyl protecting group, together with the fast formation of the iodophosphanylborane in the presence of N-iodosuccinimide. The subsequent substitution reaction was found to proceed in moderate to good yields and in a very high stereospecifity (es) using a variety of amines as nucleophiles.

Domaines: Chimie; Chimie organique

Sébastien Lemouzy, Romain Membrat, Enzo Olivieri, Marion Jean, Muriel Albalat, et al.. Umpolung Reactivity of in Situ Generated Phosphido-Boranes: An Entry to P-Stereogenic Aminophosphine-Boranes. Journal of Organic Chemistry, 2019, 84, pp.4551-4557. ⟨10.1021/acs.joc.9b00333⟩. ⟨hal-02079962⟩