title: Chiral N-phosphonyl imine chemistry: an efficient asymmetric synthesis of chiral N-phosphonyl propargylamines.
abstract: A variety of substituted chiral propargylamines have been synthesized by reacting chiral N-phosphonylimines with lithium aryl/alkyl acetylides. Seventeen examples were studied to give excellent yields (>90%) and diastereoselectivities (96 : 4 to 99 : 1). It was found that the types of bases for generating acetylides and solvents are crucial for effectiveness of this asymmetric reaction. In addition, N,N-isopropyl group on chiral N-phosphonylimine auxiliary was proven to be superior to other protecting groups in controlling diastereoselectivity.
authors.affiliation: Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas 79409-1061, USA.
authors.forename: Parminder
authors.initials: P
authors.lastname: Kaur
authors.forename: Gaurav
authors.initials: G
authors.lastname: Shakya
authors.forename: Hao
authors.initials: H
authors.lastname: Sun
authors.forename: Yi
authors.initials: Y
authors.lastname: Pan
authors.forename: Guigen
authors.initials: G
authors.lastname: Li
mesh_terms: D007097:Imines / Q000737:chemistry*; D018020:Lithium Compounds / Q000737:chemistry; D009943:Organophosphorus Compounds / Q000737:chemistry*; D010293:Pargyline / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D011437:Propylamines / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D007097:Imines; D018020:Lithium Compounds; D009943:Organophosphorus Compounds; D011437:Propylamines; C009054:propargylamine; D010293:Pargyline