Synfacts 2011(3): 0335-0335  
DOI: 10.1055/s-0030-1259466
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of β-Lactam Derivatives from a Resin-Supported Ketene

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada, Shaheen M. Sarkar
L. Méndez, E. G. Mata*
Universidad Nacional de Rosario, Argentina
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16. Februar 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).