ChemInform Abstract: Synthesis of Functionalized Cyclopropanes by MIRC Reactions of Aziridinyl‐methylenemalonates.

Abstract

Synthesis of Functionalized Cyclopropanes by MIRC Reactions ofAziridinyl-methylenemalonates.-A variety of substituents can be introduced into the resulting cyclopropane derivatives using this route. Starting from trans-substituted aziridines cis-substituted cyclopropanes are formed predominantly, whereas starting from the cis-substituted aziridine ( XIV) the trans-substituted cyclopropane (XV) is obtained. Grignard reactions catalyzed by CuCN give the most promising results. The diastereoselectivity is found to depend on the aziridine substituents as well as on the bulkiness of the reagent. -(FUNAKI, I.; BELL, R. P. L.; THIJS, L.; ZWANENBURG, B.; Tetrahedron 52 (1996) 37, 12253-12274; Dep. Org. Chem., Univ. Nijmegen, NL-6525 ED Nijmegen, Neth.; EN)