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. Author manuscript; available in PMC: 2011 Mar 19.
Published in final edited form as: Org Lett. 2010 Mar 19;12(6):1184–1187. doi: 10.1021/ol902923e

Table 1.

Amination of allyl alcohol (2 equiv) as a function of nucleophile catalyzed by a mixture of (2)AuCl (5 mol %) and AgSbF6 (5 mol %) in dioxane.

entry nucleophile product temp (°C) time (h) yield (%)a
graphic file with name nihms182257t1.jpg graphic file with name nihms182257t2.jpg
1 X = NMe (1) 60 2 99b
2 X = O 100 48 98
3 X = CH2 80 48 42
4 graphic file with name nihms182257t3.jpg graphic file with name nihms182257t4.jpg 60 24 100
5 TsNMeH graphic file with name nihms182257t5.jpg 100 24 99
RNH2 graphic file with name nihms182257t6.jpg
6 R = Ts 100 48 78
7 R = 4-MeOC6H4SO2 100 24 80c
8 R = Cbz 100 72 23
a

Isolated material of >95% purity.

b

One equivalent of allyl alcohol employed.

c

N,N-Diallyl-4-methoxybenzenesulfonamide was also isolated in 20% yield.