FIRST CATALYTIC ASYMMETRIC HYDROPHOSPHONYLATION OF CYCLIC IMINES - HIGHLY EFFICIENT ENANTIOSELECTIVE APPROACH TO A 4-THIAZOLIDINYLPHOSPHONATE VIA CHIRAL TITANIUM AND LANTHANOID CATALYSTS

The catalytic and enantioselective hydrophosphonylation of a cyclic im ine, namely the 3-thiazoline 1, is described. We have discovered a hig hly efficient enantioselective de novo approach to the pharmaceuticall y interesting 4-thiazolidinylphosphonate 2 using either titanium or la nthanoid chiral catalysts, which gives excellent enantiomeric purities (up to 98 %ee) and high chemical yields. Copyright (C) 1996 Elsevier Science Ltd