Cleavage of Chiral 4-Phenyl-2-Oxazolidinones with TMSI: Application to the Synthesis of Carbacephems

Article abstract of DOI:10.1016/S0040-4039(00)74080-9

A new technique for cleaving chiral N-substituted 4-phenyl-2-oxazolidinones is described.Thus reaction of a 7-<4-phenyl-2-oxazolidinone>carbacephem with TMSI and HMDS in acetonitrile, followed by DABCO, then aqueous hydrochloric acid gives the carbacephem nucleus, carbon dioxide, and acetophenone.This method allows a more versatile use of 4-phenyl-2-oxazolidinone as a chiral auxiliary and N-protective group in the synthesis of carbacephems. Key Words: trimethylsilyl iodide; chiral auxiliary; 4-phenyl-2-oxazolidinones; carbacephems; beta-lactams