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. Author manuscript; available in PMC: 2013 Jun 14.
Published in final edited form as: Chem Commun (Camb). 2012 May 9;48(47):5838–5840. doi: 10.1039/c2cc31973j

Table 5.

Silver-catalyzed O—H insertion of 4

graphic file with name nihms376594u5.jpg
entry R product time (h) C-4:C-6a α:βa yield (%)
1 -CH2CH3 8a 6 5:>95 12:88 42
2 -CH3 8b 8 8:92 10:90 39
3 -CH2Ph 8c 12 5:>95 5:>95 61
4 -C(CH3) 8d 10 5:>95 5:>95 46
5 -(CO)CH3 8e 16 - - <5
a

Ratio determined by 1H NMR spectroscopy of the crude reaction mixture. All reactions were run at a concentration of 0.15 M with respect to 2.

b

Isolated yield of the 8-β diastereomer