title: P-chirogenic binaphthyl-substituted monophosphines: synthesis and use in enolate vinylation/arylation reactions.
abstract: [reaction: see text] New phosphine ligands possessing both axial chirality and a chirogenic phosphorus center were prepared from (R)-2-bromo-2'-N,N-(dimethylamino)-1,1'-binaphthyl (1) via a simple Li-halogen exchange protocol. The asymmetric vinylation of a ketone enolate with (R,R(P))-2-(tert-butylphenylphosphino)-2'-N,N-(dimethylamino)-1,1'-binaphthyl (2a) afforded the coupling product with good enantiomeric excess.
authors.affiliation: Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
authors.forename: Takayuki
authors.initials: T
authors.lastname: Hamada
authors.forename: Stephen L
authors.initials: SL
authors.lastname: Buchwald
mesh_terms: D008958:Models, Molecular; D015394:Molecular Structure; D010720:Phosphines / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry*; D014961:X-Ray Diffraction
chemical_list: D010720:Phosphines; D014753:Vinyl Compounds