Substituted chiral thiophene 1-oxides and their cycloadducts of variable enantiopurity have been isolated as products of dioxygenase-catalysed sulfoxidation of the corresponding thiophenes using intact cells of Pseudomonas putida; thermal racemization (ΔG‡= 25.1 kcal mol–1) of the enantiopure metabolite (1R)-2-methylbenzo[b]thiophene 1-oxide has been observed.
D. R. Boyd, N. D. Sharma, S. A. Haughey, J. F. Malone, B. T. McMurray, G. N. Sheldrake, C. C. R. Allen and H. Dalton, Chem. Commun., 1996, 2363 DOI: 10.1039/CC9960002363
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