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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 4.

Silver-catalyzed O—H insertion of 2

graphic file with name nihms376594u4.jpg
entry R product time (h) C-4:C-6a α:βa yield (%)b
1 -CH2CH3 7a 4 10:90 15:85 41
2 -CH3 7b 4 8:92 12:88 46
3 -CH2Ph 7c 6 5:>95 22:78 39
4 -C(CH3) 7d 3 5:>95 8:92 70
5 -(CO)CH3 7e 4 5:>95 5:>95 66
6 -(CO)CH2CH3 7f 10 5:>95 11:89 71
7 -(CO)CH2Ph 7g 6 5:>95 5:>95 38
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 7-β diastereomer