Chiral N-phosphonyl imine chemistry: an efficient asymmetric synthesis of chiral N-phosphonyl propargylamines.
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.
Kaur
Parminder
P
Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas 79409-1061, USA.
Shakya
Gaurav
G
Sun
Hao
H
Pan
Yi
Y
Li
Guigen
G
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
D007097:Imines; D018020:Lithium Compounds; D009943:Organophosphorus Compounds; D011437:Propylamines; C009054:propargylamine; D010293:Pargyline