The synthesis of 4,5-disubstituted-3-amino-7-1actams from N-substituted aziridinecarboxamides is described. Bicyclic aziridine derivatives were obtained from 1-N-Boc-aziridinecarboxamides under kineucally controlled conditions. Oxiranecarboxamides showed similiar behavior and gave 3-hydroxylactams.
The synthesis of cyclopropane derivatives via a MIRC reaction of azidirinyl-methylenemalonates is described. In this way it is possible to introduce a hydrogen, a phenylthio, a tributylstannyl and an olefinic function at the cyclopropane ring, that further contains an alkylamino substituent, Addition of CuCN catalyzed Grignard reagents gave the most promising results. The diastereoselectivity was dependent on the aziridine nitrogen substituent and the bulkiness of the reagent.
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