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. 2012 Mar 26;68(21):4003–4012. doi: 10.1016/j.tet.2012.03.066

Table 1.

Oxidation of diisopropyl HPMPA (8a) to diisopropyl (S)-CPMEA (9a)

Oxidative agent; solvent Desired product Isolated yield
KMnO4/KOH; H2O 9a Complex mixture
I2/K2CO3; MeOH Methyl ester of 9a Complex mixture
RuO2/NaIO4; MeCN, CH2Cl2, H2O 9a 63%
TEMPO/BAIB; MeCN, H2O 9a 71%
TEMPO/NaClO2/NaClO; MeCN, H2O 9a 87%