Functionalized Chloroenamines in Aminocyclopropane Synthesis ‐ VII. A Diastereocomplementary Approach to Amino‐Bicyclo[n.1.0]Alkanenitriles on the Basis of Chlorinated Enamines

Abstract

AbstractReductive dechlorination of amino‐chlorobicycloalkanenitriles 5a‐c was achieved by sodium in tert.butyl alkohol/THF to give the bicyclic nitriles 6a‐c. LiAIH4 as dechlorination reagent caused a ring opening reaction with 5b,c producing diamines 7b,c. The bicyclic chloro compounds 5b,c could by obtained from enamines 1 via dichloroenamines 4. Monochlorination of 1b,c and subsequent cyclopropanation with cyanide yielded endo‐bicycloalkanenitriles 3b.c. Compounds 3 and 6 thus generally can be synthesized in a diastereocomplementary way starting from enamines 1.