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. Author manuscript; available in PMC: 2009 Sep 4.
Published in final edited form as: Org Lett. 2008 Jul 26;10(17):3817–3820. doi: 10.1021/ol801502h

Table 1.

Effect of Inorganic Bases and Organic Solvents on Epimerizationa

graphic file with name nihms118629f2.jpg
entry X R aqueous base organic solvent time/h yield/%b ee/%c
1 5 Me 1.6 equiv of 1.0 M K2CO3 0.2 M EtOAc 2.5 76 31
2 5 Me 1.6 equiv of 1.0 M NaHCO3 0.2 M EtOAc 23.0 78 65
3 5 Me 1.6 equiv of 1.5 M NaHCO3 0.2 M toluene 23.0 48 75
4 5 Me 1.6 equiv of 1.0 M K2CO3 0.2 M toluene 2.5 40 99
5 5 Me 1.6 equiv of 1.0 M K2CO3 0.2 M toluene 4.0 55 93
6 5 Me 1.6 equiv of 1.0 M K2CO3 0.2 M toluene 6.0 62 86
7 1 Et 3.2 equiv of 1.0 M K2CO3 0.16 M toluene 6.0 84 90
a

All reactions were performed with 1.6 equiv of 2 and 1.0 equiv of oxodiene.

b

Isolated yield after chromatography.

c

Determined by HPLC analysis.