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. Author manuscript; available in PMC: 2013 Jul 20.
Published in final edited form as: J Org Chem. 2012 Jul 3;77(14):6051–6058. doi: 10.1021/jo3008435

Table 1.

Optimization of olefination

graphic file with name nihms390949u1.jpg
Entry Condition (12→13) Results
1 graphic file with name nihms390949t1.jpg ~30% yield, incomplete reaction
2 TMSCH2MgBr, THF followed by NaH ~35% yield, incomplete reaction
3 CH2Br2, Zn, TiCl4 THF-CH2Cl2, 76% yield, 3 d
4 Nysted’s Reagent TiCl4, THF-CH2Cl2 88% yield, 4 h