Synthesis of optically pure 4-cyano and 4-formyl cis-β-lactams via enantiospecific Staudinger reaction

Article abstract of DOI:10.1016/S0957-4166(00)80160-3

Imines 1 and 2 derived from (+)-(1S,2S)-2-amino-1-phenylpropan-1,3-diol on cycloaddition reaction using acid chlorides (or equivalent) 3-6 in the presence of triethylamine furnished stereoselectively cis-β-lactams 7a-f in good yields. The aminols 8b,c on treatment with lead tetraacetate under different reaction conditions gave 4-cyano (9b,c) and 4-formyl (10b,c) β-lactams in high yields.