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. Author manuscript; available in PMC: 2008 Sep 8.
Published in final edited form as: J Am Chem Soc. 2006 Jan 25;128(3):925–934. doi: 10.1021/ja056150x

Table 5.

3-Phenylindole enol carbonate rearrangement

graphic file with name nihms63193f15.jpg
Entry Solvent Temp. (°C) Timea (h) ee (%)
1 CH2Cl2 23 96 73
2 THF 23 96 82
3 THF 40 18 82
4 Et2O 23 96 90
5 Et2O 35 18 83
6 toluene 23 96 87
7 toluene 40 18 74
8 t-amyl-OH 23 96 90
9 t-amyl-OH 40 18 86b
a

time required for >95% conversion of 55

b

93% isolated yield