First catalytic asymmetric hydrophosphonylation of cyclic imines: Highly efficient enantioselective approach to a 4-thiazolidinylphosphonate via chiral titanium and lanthanoid catalysts

✍ Scribed by Harald Gröger; Yoshinobu Saida; Shigeru Arai; Jürgen Martens; Hiroaki Sasai; Masakatsu Shibasaki

• Book ID: 104258725
• Publisher: Elsevier Science
• Year: 1996
• Tongue: French
• Weight: 160 KB
• Volume: 37
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(97)82944-9

✦ Synopsis

The catalytic and enantioseleetive hydrophosphonylation of a cyclic imine, namely the 3thiazoline I, is described. We have discovered a highly efficient enantioselective de novo approach to the pharmaceutically interesting 4-thiazolidinylphosphonate 2 using either titanium or lanthanoid chiral catalysts, which gives excellent enantiomeric purities (up to 98 %ee) and high chemical yields.