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. Author manuscript; available in PMC: 2012 Mar 21.
Published in final edited form as: Chemistry. 2011 Mar 1;17(13):3630–3643. doi: 10.1002/chem.201003454

Table 2.

Optmization of opening of lactone with TMS-phthalimide.

graphic file with name nihms264460u3.jpg
Entry X Y Acid Results
1 1.1 0.1 conc. H2SO4, rt 24%, 96% ee
2 1 0.2 conc H2SO4, 40 °C 32%, 97% ee
3 1 0.3 10 mol% TsOH•H2O, 40 °C 47%, 94% ee
4 1 0.2 1 equiv BSA, 10 mol% TsOH•H2O, 40 °C Full conv. in Pd-AAA; low conv. in hydrolysis step
5 2 0.2 10 mol% TsOH•H2O, 40 °C 80%, 97% ee (0.3 mmmol)
6 1.5 0.2 10 mol% TsOH•H2O, 40 °C 80%, 98% ee (3 mmol)
7 1.5 0.2 10 mol% TsOH•H2O, 40 °C 84%, 98% ee (20 mmol)