P-chirogenic binaphthyl-substituted monophosphines: synthesis and use in enolate vinylation/arylation reactions |
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Authors: | Hamada Takayuki Buchwald Stephen L |
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Institution: | Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA. |
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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. |
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