ChemInform Abstract: Functionalized Chloroenamines in Aminocyclopropane Synthesis. Part 13. Azaannulated Cyclopropanes ‐ Rigid Building Blocks for Oligoamines.

Abstract

Functionalized Chloroenamines in Aminocyclopropane Synthesis. Part 13. Azaannulated Cyclopropanes -Rigid Building Blocks for Oligoamines. -With regard to naturally occurring oligoamines, especially in terms of their interactions with DNA, structural properties are important. Thus oligoamines possessing rigid building blocks are of interest. Starting from the piperazine (I) the reaction with nucleophiles leads to different diastereomers of the title cyclopropanes. NaBH4 gives (II); the same stereochemical result is observed for cyanide or MeLi as reagents. (I) with (V) gives mainly (VI) beside (VII) and (IV). Conformation and molecular flexibility of the compounds are studied and X-ray analyses performed for (VI) and (IV). -(SEIBEL, J.; VILSMAIER, E.; FROEHLICH, K.; MAAS, G.; WAGEMANN, R.; Tetrahedron 50 (1994) 3, 715-730;