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. 2018 Jan 8;8(4):1737–1743. doi: 10.1039/c7ra12498h

Reaction scope of different allylic alcohols and aminea.

graphic file with name c7ra12498h-u1.jpg
Entry Allylic alcohols Nucleophine T (°C) Time (h) Product Yieldb (%)
1 graphic file with name c7ra12498h-u2.jpg graphic file with name c7ra12498h-u3.jpg 30 1.5 6a 91
2 4a graphic file with name c7ra12498h-u4.jpg 30 4 6b 91
3 4a graphic file with name c7ra12498h-u5.jpg 30 1.5 6c 81
4c 4a graphic file with name c7ra12498h-u6.jpg 50 26 6d 77
5 4a CH3SO2NH25e 50 7.5 6e 86
6c 4a CbzNH25f 30 2 6f 98
7c 4a graphic file with name c7ra12498h-u7.jpg 50 26 6g 93
8 4a graphic file with name c7ra12498h-u8.jpg 30 12 6h 98
9 graphic file with name c7ra12498h-u9.jpg 5a 85 53 6i, 6i′ 51 (2 : 1)d
10 4b 5b 85 53 6j, 6j′ 48 (3 : 1)d
11 graphic file with name c7ra12498h-u10.jpg 5a 50 25 6k 48
12 4c 5b 50 25 6l 42
13 graphic file with name c7ra12498h-u11.jpg 5a 50 8 6m 56
14 4d 5b 50 9 6n 70
a

Reaction conditions: 1 mmol allylic alcohols, 2 mmol nucleophile, 3d (0.05 mol% Au), 0.05 mol% AgOTf, 2 mL dioxane, argon atmosphere.

b

Isolated yield.

c

0.2 mol% 3d, 0.2 mol% AgOTf.

d

The ratio of α-product to γ-product.