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Enzymatic resolution of 5-hydroxy- and 8-hydroxy-2-tetralols using immobilized lipases

2009; Elsevier BV; Volume: 20; Issue: 4 Linguagem: Inglês

10.1016/j.tetasy.2009.02.011

1362-511X

Paolo Bonomi, Paola Cairoli, Daniela Ubiali, Carlo F. Morelli, Marco Filice, Ines Nieto, Massimo Pregnolato, Paolo Manitto, Marco Terreni, Giovanna Speranza,

Microbial Metabolic Engineering and Bioproduction

(R)-2-Tetralol (R)-2a, (R)-5-hydroxy-2-tetralol (R)-2b and (R)-8-hydroxy-2-tetralol (R)-2c, which are key intermediates in the synthesis of pharmacologically active 2-aminotetralins 3, were prepared in moderate to very high enantiomeric excess (up to 99% ee) by enzymatic resolution of the corresponding racemic butyrates rac-1a, rac-1b and rac-1c, respectively, using lipases immobilized on octyl agarose. This methodology is an alternative to the microbial reduction of 2-tetralones.