Synthesis and evaluation of P-chirogenic monodentate binaphthyl phosphines

Marie-Christine Duclos (1) , Yuttapong Singjunla (2) , Christelle Petit (2) , Alain Favre-Réguillon (2) , Erwann Jeanneau (3) , Florence Popowycz (2) , Estelle Métay (1) , Marc Lemaire (1)

1 CASYEN - Catalyse Synthèse et Environnement
2 ICBMS - Institut de Chimie et Biochimie Moléculaires et Supramoléculaires
3 UCBL - Université Claude Bernard Lyon 1

P-Chirogenic monodentate binaphthyl phosphines were prepared in five steps from enantiomerically pure BINOL. This approach supposes the utilization of two methods previously developed in our group, the formation of secondary phosphine oxide, and the reduction of tertiary phosphine oxide using the association of tetramethyldisiloxane and Ti(OiPr)4. During the last reduction step, only the formation of the more stable diastereoisomer was observed. This product was employed as a ligand for the palladium catalyzed hydrosilylation of styrene to afford the corresponding alcohol with high yield and enantiomeric excess.

Mots clés: Catalysis; P-chirogenic; Phosphine; TMDS; Hydrosilylation

Domaines: Chimie organique

Marie-Christine Duclos, Yuttapong Singjunla, Christelle Petit, Alain Favre-Réguillon, Erwann Jeanneau, et al.. Synthesis and evaluation of P-chirogenic monodentate binaphthyl phosphines. Tetrahedron Letters, 2012, 53 (45), pp.5984-5986. ⟨10.1016/j.tetlet.2012.07.136⟩. ⟨hal-01176238⟩