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. Author manuscript; available in PMC: 2012 Jun 15.
Published in final edited form as: J Am Chem Soc. 2011 May 23;133(23):9104–9111. doi: 10.1021/ja202706g

Table 3.

Oxidation of simple bis(indoles) with peptide 22 as a catalyst.

graphic file with name nihms298984t14.jpg
entry bis-indole hydroxy-indoleninea R1 R2 yield (%) er
1 40a 41a graphic file with name nihms298984t15.jpg H 77 86:14
2 40b 41b graphic file with name nihms298984t16.jpg H 87 83:17
3 40c 41c graphic file with name nihms298984t17.jpg 89 82:18 (95:5)b
4 graphic file with name nihms298984t18.jpg graphic file with name nihms298984t19.jpg 70 93:7
a

Reaction conditions for indole oxidation: indole (1.0 equiv), peptide (10 mol%), and DMAP (5 mol%) in CHCl3 (0.1 M) at 0 °C, then add aq. H2O2 (1.2 equiv), and DIC (1.2 equiv).

b

Recrystallized to 95:5 er from 95/5 2-propanol/ethanol mixture (yield after recrystallization 47%).

DMAP = N,N-dimethyl-4-aminopyridine, DIC = diisopropylcarbodiimide, Phth = phthaloyl, SES = 2-(trimethylsilyl)ethylsulfonyl.