Fe-Catalyzed cross-coupling of 3-chloroprop-2-en-1-ylamines with PhMgBr in the presence of TMEDA
A stereoselective synthesis of ( E )- and ( Z )-3-phenylprop-2-en-1-ylamines based on Fe(acac)3/ТМEDА catalyzed cross-coupling of stereochemically pure 3-chloroprop-2-en-1-ylamines with PhMgBr was developed. Initial 3-chloroprop-2-en-1-ylamines were obtaining by allylation of amines by available isomers of 1,3-dichlopropene. The cross-coupling of PhMgBr with stereochemically pure ( E )- and ( Z )-isomers of 1-(3-chloroprop-2-en-1-yl)piperidine and 4-(3-chloroprop-2-en-1-yl)morpholine in the presence of 1% mol Fe(acac)3 and 5% mol ТМEDА in THF affordes corresponding isomers of 1-(3-phenylprop-2-en-1-yl)piperidine and 4-(3-phenylprop-2-en-1-yl)morpholine in high yields.