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. Author manuscript; available in PMC: 2013 Feb 17.
Published in final edited form as: J Org Chem. 2012 Jan 26;77(4):1891–1908. doi: 10.1021/jo202366c

Table 3.

Optimization of Oxidative Nazarov Cyclization.a

graphic file with name nihms354218t3.jpg
Entry solvent oxidant temp ratio (15a:21)
1 DCM / hexane (1:1) m-CPBA (1 equiv.) r.t. 1: 1.2
2 toluene m-CPBA (1 equiv.) r.t. 1: 4
3 DMF m-CPBA (1 equiv.) r.t. 1.6: 1
4 DMF m-CPBA (1 equiv.) p-TSA (5 mol %) −10 – 0 °C 1: 2
5 DMF m-CPBA (3.5 equiv.) 0 °C 4.3: 1
6 DMF CF3CO3H −10 – 0 °C 1: 6
7 sulfolane m-CPBA (3.5 equiv.) −10 – 0 °C 1.2: 1