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. 2014 Sep 24;16(19):5188–5191. doi: 10.1021/ol502551u

Table 2. Optimization of the Cycloisomerization of 4aa.

graphic file with name ol-2014-02551u_0006.jpg

entry catalyst solvent t (min) yield (%)b
1 PPh3AuCl/AgNTf2 toluene 60 c
2 AgNTf2 toluene 30 79
3 AgNTf2 THF >240 c
4 AgNO3 toluene 40 91
5 Ag2CO3 toluene 40 97
6 AgOAc toluene 40 94
7 AgOTf toluene 50 91
8 AgSbF6 toluene 30 91
9 CuI toluene >1 d traces
10 PtCl2 toluene >1 d traces
11 Ag2CO3 toluene/THF 4:1 4 h 94
12d Ag2CO3 toluene 40 97
a

Reaction conditions: 0.13 mmol of 3a, 10 mol % of catalyst, 1.3 mL solvent, rt.

b

Yield of isolated 4a after flash column chromatography.

c

Complicated mixture of products which could not be separated.

d

In the presence of 20 mol % A and 40 mol % (S)-N-Boc alanine.