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. Author manuscript; available in PMC: 2010 Jan 8.
Published in final edited form as: Angew Chem Int Ed Engl. 2009;48(34):6328–6331. doi: 10.1002/anie.200902420

Table 3.

Alkylation of Electron-Deficient Indoles

graphic file with name nihms162524u4.jpg
Entry R n Time Product Yield (%)[a] ee (%)
1 4-F 1 36 h 2m 57 96 (99)[b]
2 4-Br 1 5 d 2n 47 97
3 5-F 1 48 h 2o 87 94
4 5-Br 1 5 d 2p 80 93
5 6-F 1 72 h 2q 75 96
6 6-Cl 1 96 h 2r 81 96
7 4-Br 2 5 d 2s 12 85
8 6-F 2 72 h 2t 75 96
9 6-Cl 2 5 d 2u 40 92
[a]

Isolated yield

[b]

Ee of product purified by trituration from Et2O in parenthesis.