Synthesis and evaluation of P-chirogenic monodentate binaphthyl phosphines
摘要:
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((OPr)-Pr-i)(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. (C) 2012 Published by Elsevier Ltd.
Synthesis and evaluation of P-chirogenic monodentate binaphthyl phosphines
摘要:
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((OPr)-Pr-i)(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. (C) 2012 Published by Elsevier Ltd.
Synthesis of P-stereogenic BINAP bissulfide analogues
作者:Eoin Rafter、Jimmy Muldoon、Helge Müller Bunz、Declan G. Gilheany
DOI:10.1016/j.tetasy.2011.09.007
日期:2011.9
A synthetic route to BINAP disulfide analogues with chirality on one of the phosphorus atoms was developed. The synthesis of these ligands was achieved by step-wise palladium and nickel-catalysed coupling reactions of the precursor binaphthyl triflate with secondary phosphines and phosphine oxides, respectively. C2-Unsymmeric BINAP bissulfide analogues with the same aryl substituents were also synthesized for the sake of comparison. Preliminary studies of the reduction of these sulfides to the free phosphines are also described. (C) 2011 Elsevier Ltd. All rights reserved.