A direct synthesis of 1-aryl- and 1-alkenylcyclopropylamines from aryl and alkenyl nitriles
The reaction of various aromatic nitriles with 1.1 equiv of Ti(Oi-Pr)4 and 2.2 equiv of EtMgBr followed by addition of a Lewis acid gave 1-aryl cyclopropylamines in 43-76% yields. Under similar conditions, conjugated alkene-nitriles afford 1-alkenylcyclopropylamines (42-65%).
Bertus, Philippe,Szymoniak, Jan
p. 7133 - 7136
(2007/10/03)
Regioselective palladium (0) catalyzed azidation and amination of 1-alkenylcyclopropyl esters: A new route to 2,3-methanoamino acids
Palladium (0) catalyzed azidation of 1-alkenylcyclopropyl esters provides regioselectively 1-azido-1-alkenyl cyclopropanes, convenient precursors of 2,3-methanoamino acids. On the other hand, amination occurred exclusively on the less substituted allylic end, providing strained 2-cyclopropylideneethylamine derivatives.