Nucleophilic substitution of protected β-bromoethyl cyclohexadiene-cis-diol as an alternative to direct microbial oxidation of β-functionalized phenethyl substrates
Abstract
(5S,6R)-1-(2-Bromoethyl)-5,6-(propane-2,2-diyldioxy)cyclohexa-1,3-diene 6 is subjected to nucleophilic substitution reaction using C-, N-, O- and S-based nucleophiles. The yields of the products are compared with those obtained by direct microbial oxidation of the corresponding aromatic substrates. The enantiomeric excess and isolated yield for each compound are reported.