Synthesis of functionalized cyclopropanes by MIRC reactions of aziridinyl-methylenemalonates

Article abstract of DOI:10.1016/0040-4020(96)00712-0

The synthesis of cyclopropane derivatives via a MIRC reaction of aziridinyl-methylene-malonates 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.