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. Author manuscript; available in PMC: 2011 Nov 10.
Published in final edited form as: J Am Chem Soc. 2010 Nov 10;132(44):15752–15765. doi: 10.1021/ja106837b

Table 2.

Carbonate Opening Experiments

graphic file with name nihms247258u2.jpg
entry Aryl carbonate acid, equiv ether conv.,a% e.r.b e.s. (%)
1c 4-MeOC6H4 25b TFA, 0.1 28b 46 52.5:47.5 5
2c Ph 25a TFA, 0.1 28a 17 57.4:42.6 17
3c 2,4,6-(i-Pr)3C6H2 25c TFA, 0.1 28c 48 62.8:37.2 30
4c 4-CF3C6H4 25d TFA, 1.0 28d 100 61.8:38.2 27
5c 2-CF3C6H4 25e TFA, 1.0 28e 100 67.2:32.8 40
6c 4-NO2C6H4 25f TFA, 1.0 28f 54 93.6:6.4 >99
7d 2,6-(CF3)2C6H3 25g MsOH, 1.0 28g 94 93.7:6.3 >99
a

Conversion determined by monitoring reaction progress by 1H NMR spectroscopy.

b

Determined by CSP-SFC analysis.

c

Reaction time was 24 h.

d

Reaction time was 2 h.