title: Stereoselective synthesis of P-stereogenic aminophosphines: ring opening of bulky oxazaphospholidines.
abstract: A highly diastereoselective and efficient synthesis of P-stereogenic bulky alkyl and aryl aminophosphines that relies on ring opening of tert-butyl-oxazaphospholidine 2 is described. Ring opening with several organometallic reagents takes place with inversion of configuration at the phosphorus center as it has been demonstrated by X-ray analysis of two ring-opened intermediates. The unprecedented reactivity observed is attributed to the presence of a free NH functionality that facilitates the attack of the organometallic reagent in an S(N)2@P-type process.
authors: Unitat de Recerca en Síntesi Asimètrica (URSA-PCB), Institute for Research in Biomedicine and Departament de Química Orgànica, Universitat de Barcelona, C/Baldiri Reixac 10, E-08028 Barcelona, Spain.
authors: Thierry
authors: T
authors: León
authors: Antoni
authors: A
authors: Riera
authors: Xavier
authors: X
authors: Verdaguer
mesh_terms: D000588:Amines / Q000138:chemical synthesis / Q000737:chemistry*; D008958:Models, Molecular; D010720:Phosphines / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000588:Amines; D010720:Phosphines