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. 2015 Mar 10;137(10):3510–3519. doi: 10.1021/ja503899t

Table 1. Selected Conditions for the Cyclization of 20.

graphic file with name ja-2014-03899t_0004.jpg

entry conditions result
1 t-BuLi; THF; −78 °C → rt metal–halogen exchange
exclusively
2 i-PrMgCl; THF; −78 °C → rt metal–halogen exchange
exclusively
3 t-BuLi, ZnCl2, Ti(OiPr)4, etc.; THF;
–78 °C → rt		 metal–halogen exchange
exclusively
4 t-BuLi, BF3·OEt2, TiCl4, Et2AlCl, etc.;
THF; –78 °C		 skeletal rearrangement
5 t-BuLi, CuI or CuBr or CuCN, etc.; THF;
–78 °C → rt		 metal–halogen exchange
exclusively