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. 2012 Nov 6;1(6):245–250. doi: 10.1002/open.201200037

Table 1.

Different activators in the rearrangement of 1 a[a]

Inline graphic

Entry Activator 2 aYield [%] 3 aYield [%]
1 0 0
2 TMSOTf 93 0
3 TBDMSOTf 88 0
4 BF3⋅OEt2 18 67
5[b] camphorsulfonic acid 0 92
6[c] TsOH⋅H2O 8 64
[a]

Reagents and conditions: a) PhI(OCOCF3)2 (1 equiv), activator (2 equiv), MeCN, RT, 30 min;

[b]

When the reaction was performed by using substrate (E)-1 f, rearranged product 3 f was obtained in 89 % yield.

[c]

Koser’s reagent Ph(OH)OTs was used for this reaction. In addition to 2 a and 3 a, compound 4 a was observed in 8 % yield.