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Synthesis of β-Lactam Derivatives from a Resin-Supported Ketene
L. Méndez, E. G. Mata*
Universidad Nacional de Rosario, Argentina
16 February 2011 (online)
β-Lactams 7 were prepared from an in situ generated Wang resin supported ketene 5 and 3,4-dihydroisoquinolines 4. Thus, a resin-supported aryloxyacetic acid 3 was prepared from Wang resin and 1 in two steps. The Staudinger cycloaddition of 4 and 5, in situ generated from 3 with Mukaiyama’s reagent, afforded resin-supported β-lactams 6. Detachment of the resin moiety with TFA gave multicyclic carbacepham analogues 7a-e in 55-77% yield (5 examples).