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. Author manuscript; available in PMC: 2013 Jun 19.
Published in final edited form as: J Am Chem Soc. 2008 Jan 4;130(4):1440–1452. doi: 10.1021/ja0773507

Table 5.

Catalyst Optimization for Cycloisomerization of Bromoallenyl Ketone 20a

graphic file with name nihms382578u5.jpg

entry cat. (mol %) solvent time GC yield, % (21a:22a)
1 CuCl (10) toluene 1 day 29 (21a only)
2 CuI (10) toluene 1 day 21 (21a only)
3 AgBF4 (5) DCM 1 day traces
4 PtCl2 (5) toluene 3h 50 (96:4)
5 AuCl3 (1) toluene 5 min 86 (95:5)
6 AuCl3 (1) THF 5 min 78 (5:95)
7 Au(PPh3)Cl (1) toluene 9h N/D (16:84)
8 Au(PEt3)Cl (1) toluene 9h N/D (< 1:99)
9 AlCl3 (50) toluene 16 h 27 (21a only)
10 SiO2 toluene 16 h 21 (21a only)