Cw. Jefford et G. Timari, AMPLIFIED ASYMMETRIC DIHYDROXYLATION OF A RACEMIC CYCLOPENTENE, Journal of the Chemical Society, Chemical Communications, (15), 1995, pp. 1501-1502
Racemic cyclopenteno-1,2,4-trioxane 1/ent-1 by iterative dihydroxylati
on with N-methylmorpholine N-oxide in the presence of catalytic amount
s of K2OsO4 and (DHOD)(2)PHAL in aqueous Me(2)CO at 25 degrees C gives
essentially enantiomerically pure diols 2 (96% e.e.) and ent-2 (98% e
.e.) in yields of 31.5 and 43%, respectively.