Racemic cyclopenteno-1,2,4-trioxane 1/ent-1 by iterative dihydroxylation with N-methylmorpholine N-oxide in the presence of catalytic amounts of K2OsO4 and (DHQD)2PHAL in aqueous Me2 CO at 25 °C gives essentially enantiomerically pure diols 2(96% e.e.) and ent-2(98% e.e.) in yields of 31.5 and 43%, respectively.
C. W. Jefford and G. Timári, J. Chem. Soc., Chem. Commun., 1995, 1501 DOI: 10.1039/C39950001501
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