Single enantiomer 2-hydroxy-3-butenyl tosylate is a key precursor for single enantiomer 3,4-epoxy-1-butene and 3-butene-1,2-diol. The epoxide results from ring-closure of the hydroxy-tosylate while the diol is obtained through the intermediacy of the corresponding cyclic carbonate. This latter sequence avoids the loss of enantiomeric purity observed through direct hydrolysis.
epoxides - asymmetric synthesis - chirality - diols - nucleophiles
