Direct Synthesis of β‑Hydroxy-α-amino Acids <i>via</i> Diastereoselective Decarboxylative Aldol Reaction

A straightforward metal-free synthesis of <i>anti</i>-β-hydroxy-α-amino acids is described. The organic base-mediated decarboxylative aldol reaction of cheap, readily available α-amidohemimalonates with various aldehydes afforded under very mild conditions <i>anti</i>-β-hydroxy-α-amido esters in high yields and complete diastereoselectivity. Simple one-pot subsequent transformations enabled the corresponding <i>anti</i>-β-hydroxy-α-amino acids or in a few examples their <i>syn</i> diastereomers to be obtained directly using epimerization conditions

Synthesis and evaluation of P-chirogenic monodentate binaphthyl phosphines

International audienceP-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