Table 1.

Optimization of the Domino Cu-Catalyzed Amidation/Cyclization Reaction

entry	Y	base	solvent	yield 3aa	yield 4a	yield 5a
1b	I (1a)	Cs2CO3	THF	6%	-	14%
2	1a	Cs2CO3	THF	37%	23%	-
3	1a	Cs2CO3	1,4-dioxane	35%	11%	6%
4	1a	Cs2CO3	toluene	3%	-	11%
5c	1a	Cs2CO3	THF	40%	31%	-
6	1a	K3PO4	THF	9%	23%	14%
7	1a	K2CO3	THF	-	-	33%
8	Cl (1b)	Cs2CO3	THF	87%		-
9	OMs (1c)	Cs2CO3	THF	89%d	-	-

^aGC yield with dodecane as an internal standard; 99% conversion of 1, unless indicated otherwise.

^bExperiment performed at rt; 41% conversion of 1a.

^cRacemic trans-1,2-N,N′-dimethylcyclohexanediamine was used as a ligand.

^dIsolated yield.