Synthesis and evaluation of P-chirogenic monodentate binaphthyl phosphines |
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Authors: | Marie-Christine DuclosYuttapong Singjunla Christelle PetitAlain Favre-Réguillon Erwann JeanneauFlorence Popowycz Estelle MétayMarc Lemaire |
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Institution: | a Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, UMR-CNRS 5246, Equipe Catalyse Synthèse Environnement, Université de Lyon, Université Claude Bernard-Lyon 1, Bâtiment Curien, 43 Bd du 11 novembre 1918, F-69622 Villeurbanne Cedex, France b Centre de Diffractométrie Henri Longchambon, Université Claude Bernard Lyon1, 43 Bd du 11 novembre 1918, 69622 Villeurbanne cedex, France |
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Abstract: | 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. |
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Keywords: | Phosphine TMDS Catalysis P-chirogenic Hydrosilylation |
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