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. Author manuscript; available in PMC: 2016 Jun 3.
Published in final edited form as: Tetrahedron Lett. 2015 Jan 27;56(23):3273–3276. doi: 10.1016/j.tetlet.2015.01.120

Table 2.

Scope of the reaction of the allene 1a with various sulfonamide 2.a

graphic file with name nihms658835u2.jpg
Entry R Time (h) 3 Yield (%)b E/Zc
1 H 12 3a 95 93:7
2 4-Me 12 3b 96 93:7
3 4-MeO 24 3c 93 94:6
4 4-Br 12 3d 95 94:6
5 4-Cl 9 3e 96 93:7
6 4-F 7 3f 98 94:6
7 4-NO2 30 3g 92 90:10
8 3-Me 10 3h 95 94:6
9 3-Br 8 3i 93 93:7
10 3-Cl 9 3j 88 96:4
11 3-NO2 24 3k 88 89:11
12 2-NO2 26 3l 82 99:1
13 2-Me 16 3m 94 91:9
14 2-Cl 10 3n 97 96:4
15 2-F 9 3o 96 91:9
16 2-CO2Me 24 3p 92 94:6
17 2,6-di-Cl 8 3q 91 95:5
18 graphic file with name nihms658835t1.jpg
(2r)
8 3r 81 93:7
a

Reactions of 1a (0.3 mmol) and 2 (0.2 mmol) were performed in Et2O (2 mL) at room temperature.

b

Isolated yield based on 2.

c

Determined using 1H NMR spectroscopy.