P-chirogenic binaphthyl-substituted monophosphines: synthesis and use in enolate vinylation/arylation reactions.
[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.
Hamada
Takayuki
T
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Buchwald
Stephen L
SL
D008958:Models, Molecular; D015394:Molecular Structure; D010720:Phosphines / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry*; D014961:X-Ray Diffraction
D010720:Phosphines; D014753:Vinyl Compounds