1187429-39-5Relevant academic research and scientific papers
Merging nucleophilic and hydrogen bonding catalysis: An anion binding approach to the kinetic resolution of propargylic amines
Klauber, Eric G.,De, Chandra Kanta,Shah, Tejas K.,Seidel, Daniel
supporting information; experimental part, p. 13624 - 13626 (2010/11/17)
An efficient kinetic resolution of primary propargylic amines with s-factors of up to 56 is reported. The strategy is based on a dual catalytic approach, namely the use of a newly developed and easy-to-make thiourea-amide anion binding catalyst in combination with 4-(dimethylamino)pyridine (DMAP), both employed at a 5 mol % catalyst loading. Benzylic amines are also resolved with s-factors of up to 38.
Chiral N-phosphonyl imine chemistry: An efficient asymmetric synthesis of chiral N-phosphonyl propargylamines
Kaur, Parminder,Shakya, Gaurav,Sun, Hao,Pan, Yi,Li, Guigen
experimental part, p. 1091 - 1096 (2010/06/20)
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. The Royal Society of Chemistry.
