Chiral arene hydrates of naphthalene: enzymatic and chemical syntheses

Abstract

Bacterial metabolism of the dihydronaphthalenes 1 or 3 using cultures of Pseudomonas putida UV4 yielded the arene hydrates of naphthalene 2 or a mixture of 4 and 5 respectively; these arene hydrates have also been obtained in homochiral form either by synthesis from enantiomerically pure alcohols 10 and 12 and arene oxide 11 precursors or by chiral stationary phase HPLC separation of arene hydrate enantiomers.