Table 3.

Tunable Amination of Homoallenic Carbamates

entry	allene	AgOTf:phena,b	d	yield 4	5
1	3a	1:1.25		79%	<4%
		1:3		0%	81%
		Rh2(esp)2		35%	17%
2	3b	1:1.25		79%	13%
		1:3		1%	76%
3	3c	1:1.25		80%	9%
		1:3		0%	76%
		Rh2(esp)2		34%	34%
4	3d	1:1.25		72%	18%
		1:3		5%	65%
		1:3e		<1%	71%
5	3e	1:1.25c		67%	18%
		1:3		0%	83%
6	3f	1:1.25		87%	7%
		1:3		0%	88%
		Rh2(esp)2		34%	44%
7	3g	1:1.25		70%	4%
		1:3		0%	78%
8	3h	1:1.25		57%	12%
		1:3		4%	74%
		1:3e		<1%	68%
9	3i	1:1.25		61%	0%
		1:3		3%	74%
		1:3e		<1%	71%
10	3j	1:1.25		58%	0%
		1:3		0%	36%
		1:3e		2%	62%

^aAziridination: 20 mol % AgOTf, 25 mol % phen, 2 equiv PhlO, 4 Å MS, CH₂Cl₂.

^bC–H insertion: 10 mol % AgOTf, 30 mol % phen, 3.5 equiv PhIO, 4 Å MS, CH₂Cl₂.

^c2,2′-bipyridine ligand.

^dI = insertion. A = aziridination,

^e10 mol % BHT added