A highly chemo- and diastereoselective protocol toward amino-substituted donor-acceptor cyclopropanes via the formal nucleophilic displacement in bromocyclopropanes is described. A wide range of N-nucleophiles, including carboxamides, sulfonamides, azoles, and anilines, can be efficiently employed in this transformation, providing expeditious access to stereochemically defined and densely functionalized cyclopropylamine derivatives.

Formal Substitution of Bromocyclopropanes with Nitrogen Nucleophiles. -The formation of cyclopropanes catalyzed by 18-crown-6 gives products with high diastereoselectivity. -(BANNING, J. E.; GENTILLON, J.; RYABCHUK, P. G.; PROSSER, A. R.; ROGERS, A.; EDWARDS, A.; HOLTZEN, A.; BABKOV, I. A.; RUBINA, M.; RUBIN*, M.; J. Org. Chem. 78 (2013) 15, 7601-7616, http://dx.doi.org/10.1021/jo4011798 ; Dep. Chem., Univ. Kans., Lawrence, KS 66045, USA; Eng.) -S. Adam 51-055