Abstract
Asymmetric dihydroxylation (AD) of a racemic mixture of 1-acyloxy-2( E)-alkenylphosphonates with AD- mix-α or -β reagents was examined. The kinetic rate of dihydroxylation was highly dependent upon the configuration of the 1-acyloxy functional group as well as the nature of substituents at the 3-position. The reaction of a racemic mixture of diethyl ( E)-3-phenyl-1-acetyloxy-2-propenylphosphonate with an AD- mix-β reagent preferentially dihydroxylated the R-enantiomer to leave an unreacted S-enantiomer of high enantiomeric purity. Double diastereoselection of the resolved diethyl 3-phenyl-1-acetyloxy-2( E)-propenylphosphonate in dihydroxylation was also examined.
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