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. Author manuscript; available in PMC: 2008 Sep 15.
Published in final edited form as: J Am Chem Soc. 2007 Jul 21;129(32):9868–9878. doi: 10.1021/ja072446m

Table 3.

Sequential [3,3]/1,2-acyloxy migration/cycloisomerization

graphic file with name nihms-62600-t0030.jpg
entry substrate 39 cat. time, min product 40 yield, %a
1 graphic file with name nihms-62600-t0031.jpg b AgBF4 2 graphic file with name nihms-62600-t0032.jpg >99
2 graphic file with name nihms-62600-t0033.jpg c AgBF4 180 graphic file with name nihms-62600-t0034.jpg 73b
3 TMSOTf 600 70b
4 graphic file with name nihms-62600-t0035.jpg d AgBF4 15 graphic file with name nihms-62600-t0036.jpg 73
5 graphic file with name nihms-62600-t0037.jpg e AgBF4 15 graphic file with name nihms-62600-t0038.jpg 84
6 graphic file with name nihms-62600-t0039.jpg f AgBF4 15 graphic file with name nihms-62600-t0040.jpg 90
7 graphic file with name nihms-62600-t0041.jpg g AgBF4 10 graphic file with name nihms-62600-t0042.jpg 86
8 graphic file with name nihms-62600-t0043.jpg a Cu(OTf)2 15 graphic file with name nihms-62600-t0044.jpg 60c
9 graphic file with name nihms-62600-t0045.jpg h Cu(OTf)2 180 graphic file with name nihms-62600-t0046.jpg 81b
10 graphic file with name nihms-62600-t0047.jpg i AuCl3 15 graphic file with name nihms-62600-t0048.jpg 78b,c
11 graphic file with name nihms-62600-t0049.jpg j Cu(OTf)2 15 graphic file with name nihms-62600-t0050.jpg 91c
a

Run on 1.0 mmol scale.

b

Run on 0.5 mmol scale.

c

Run in toluene.