Uses
(1R,2R)-(-)-N-p-Tosyl-1,2-diphenylethylenediamine is used as a catalyst in stereoselective preparation of aromatic ketone derivatives as well as other chiral organic compounds.
Synthesis
(1) (R,R)-1,2-diphenylethylenediamine (20 mmol) was dissolved in dichloromethane (30 mL) and cooled to 0°C in an ice bath. A solution of p-toluenesulfonyl chloride (20 mmol) dissolved in dichloromethane (30 mL) was slowly added dropwise to the above solution at 0 °C (dropwise time 30 min). After the dropwise addition was completed, the reaction was continued at 0°C for 1 hour. After completion of the reaction, the solvent was removed by concentration under reduced pressure by rotary evaporator to obtain the crude product. The crude product was purified by column chromatography (eluent: dichloromethane/methanol=10:1, v/v) to afford the target product (R,R)-(-)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine (15 mmol) in 75% yield.
References
[1] Tetrahedron Letters, 2008, vol. 49, # 27, p. 4289 - 4291
[2] European Journal of Organic Chemistry, 2000, # 12, p. 2247 - 2252
[3] Tetrahedron Asymmetry, 2009, vol. 20, # 6-8, p. 910 - 920
[4] Molecules, 2010, vol. 15, # 4, p. 2551 - 2563
[5] Patent: CN107286089, 2017, A. Location in patent: Paragraph 0078; 0148-0149
