Table 1.

Scope of Ynamide-Kinugasa Reaction

entry	ynamides		α-amino-β-lactams		yield [%]a	dr: [a:b]b
1		7		12: R = Ph	80	≥95:5
2		8		13: R = i-Pr	36	≥ 95:5
3		9		14: R = CHPh2	28c,d	nde
4		7		15: R1 = 4-Br-Ph	77	≥95:5
5		7		16: R1 = 1Naph	71	90:10
6		7		17: R1 = styryl	72c,f	93:7
7		7		18: X = O	61c	82:18
8		7		19: X = S	60c,g	≥95:5
9		7		20: X = Cl	65	≥95:5
10		7		21: X = CO2Et	63	≥95:5
11		5		22: R = Bn; R1 = Ph	59h	91:9
12		7		23: R = Ph; R1 = Ph	60h	≥95:5
13		7		24: R = Ph; R1 = c-hex	60c,i,h	92:8
14		10		25	61	≥95:5
15		11		26	60c,h	≥95:5

^aReaction conditions are as shown in Scheme 2 unless otherwise indicated. All are isolated yields.

^bdr is determined using ¹H NMR. All isomers-a are cis. The minor isomer-b is trans.

^c0.2 equiv of CuI was used, and the reaction was run at 0 °C to rt.

^dWith 0.2 equiv of CuCl, the yield was 13%.

^end: Not determined.

^fWith 0.2 equiv of CuCl, yield was 71% and dr = 91:9.

^gWith 0.2 equiv of CuCl, yield was 48% and dr = 86:14.

^hPMP: para-methoxyphenyl.

ⁱWith 0.2 equiv of CuCl and 4.8 equiv of Hünig's base, yield was 54% and dr = 87:13.