New chiral synthons from the microbial oxidation of bromonaphthalenes

Article abstract of DOI:10.1016/0957-4166(95)00421-1

1-Bromo- and 2-bromonaphthalene were subjected to bio-oxidation with whole cells of Pseudomonas putida NCIB 9816-11. The major metabolites were isolated and spectroscopically characterized as (+)-cis-(1R,2S)-Dihydroxy-1,2-dihydro-8-bromonaphthalene 1, (+)-cis-(1R,2S)-Dihydroxy-1,2-dihydro-5-bromonaphthalene 2 from 1-bromonaphthalene and (+)-cis-(1R,2S)-Dihydroxy-1,2-dihydro-7-bromonaphthalene 8 from 2-bromonaphthalene. The absolute stereochemistry and enantiomeric excess were determined by conversion of each metabolite to the known (-)-cis-tetrahydronaphthalene diol 6.