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. Author manuscript; available in PMC: 2014 Aug 8.
Published in final edited form as: Org Lett. 2008 Jun 14;10(14):3049–3052. doi: 10.1021/ol8010248

Table 2.

Substrate scope of PhF5CO2H (9) in BV reaction.

entry ketone lactone yielda
1 graphic file with name nihms609684t1.jpg graphic file with name nihms609684t2.jpg 96%
2 graphic file with name nihms609684t3.jpg graphic file with name nihms609684t4.jpg 75%
3 graphic file with name nihms609684t5.jpg graphic file with name nihms609684t6.jpg 78%
4 graphic file with name nihms609684t7.jpg graphic file with name nihms609684t8.jpg 48%
5 graphic file with name nihms609684t9.jpg graphic file with name nihms609684t10.jpg 78%
6b graphic file with name nihms609684t11.jpg graphic file with name nihms609684t12.jpg 23%
7c graphic file with name nihms609684t13.jpg graphic file with name nihms609684t14.jpg 10%
a

Yield was measured by comparison to an internal NMR standard, or by isolation of the product by chromatography. Except where noted, DIC was always added at 1.2 DIC equiv/h.

b

Reaction run with 4 equiv DIC (Rate of additions 0.5 DIC equiv/h), 5 equiv aq H2O2 and DMAP (0.1 equiv) for 8 h.

c

DIC was added at 0.6 DIC equiv/h for 6 h.