ChemInform Abstract: Functionalized Chloroenamines in Aminocyclopropane Synthesis. Part 7. A Diastereocomplementary Approach to Aminobicyclo(n.1.0)alkanenitriles on the Basis of Chlorinated Enamines.

Abstract

Functionalized Chloroenamines in Aminocyclopropane Synthesis. Part 7.A Diastereocomplementary Approach to Aminobicyclo(n.1.0)alkanenitriles on the Basis of Chlorinated Enamines.-Chloroenamines (II) and (V) are selected as representative compounds to test the diastereoselectivity of the cyanide-induced cyclopropanation reaction. While (II) gives endo-bicycloalkanenitriles (III), the dichloroenamines (V) lead to an exo-morpholino system (VI), which is dechlorinated to give (VII), the exo isomers of (IV). The use of LiAlH4 as reductive agent causes ring opening of (VI) besides the expected reduction of the CN group. -(VILSMAIER, E.; STAMM, T.; DAUTH, W.; TETZLAFF, C.; BARTH, S.; Bull. Soc. Chim.