Palladium-catalysed O -Allylation of α-Hydroxyphosphonates: An Expedient Entry into Phosphono-oxaheterocycles

Mansour Dolé Kerim (1) , Martin Cattoen (2) , Nicolas Fincias (1, 2) , Aurélie Dos santos (1) , Stellios Arseniyadis (2) , Laurent El Kaim (1)

1 DCSO - Laboratoire de synthèse organique
2 School of Biological and Chemical Sciences, Queen Mary University of London

We report here an unprecedented palladium‐catalysed O‐allylation of α‐hydroxyphosphonates. The method was eventually included in a sequential Pudovik/Tsuji‐Trost type O‐allylation/Ring‐Closing Metathesis to afford a variety of phosphorylated heterocycles of various sizes ranging from 5 to 16 starting from readily available aldehydes.

Keywords: α-Hydroxyphosphonates; O-allylation; Palladium; Pudovik reaction; Ring-closing metathesis; Metacyclophanes

Domains: Chemical Sciences; Organic chemistry

Mansour Dolé Kerim, Martin Cattoen, Nicolas Fincias, Aurélie Dos santos, Stellios Arseniyadis, et al.. Palladium-catalysed O -Allylation of α-Hydroxyphosphonates: An Expedient Entry into Phosphono-oxaheterocycles. Advanced Synthesis and Catalysis, 2018, 360 (3), pp.449-454. ⟨10.1002/adsc.201701150⟩. ⟨hal-02091718⟩