Table 5.

Initial Examination of Conditions for Enantioselective Enyne Hydroamination^a

entry	additive	Et3N (Y/N)	solvent	yield of 2a (%)b	2a:9c	er of 2ad
1	NaBF4	N	CH2Cl2	<2	–	–
2e	NaBF4	N	CH2Cl2	56	4:1	53.5:46.5
3	NaBF4	Y	CH2Cl2	<2	–	–
4e	NaBF4	Y	CH2Cl2	71	19:1	63:37
5e	NaBArF4	N	Et2O	73	13:1	69.5:30.5
6	NaBArF4	Y	Et2O	48–73f	>20:1	<52:48–74:26f
7	NaBArF4	Y	CH2Cl2	65–70f	>20:1	54:46–82:18f

^aSee Table 1.

^bIsolated yield of 2a (single data point unless otherwise noted).

^cDetermined by 400 MHz ¹H NMR analysis of the unpurified mixture.

^dDetermined by HPLC analysis (single data point unless otherwise noted).

^ePerformed with isolated catalyst; see the Supporting Information.

^fRange for three experiments.