(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.
Enzymatic resolution of 5-hydroxy- and 8-hydroxy-2-tetralols using immobilized lipases / P. Bonomi, P. Cairoli, D. Ubiali, C. F. Morelli, M. Filice, I. Nieto, M. Pregnolato, P. Manitto, M. Terreni, G. Speranza. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 20:4(2009), pp. 467-472. [10.1016/j.tetasy.2009.02.011]
Enzymatic resolution of 5-hydroxy- and 8-hydroxy-2-tetralols using immobilized lipases
P. BonomiPrimo
;P. CairoliSecondo
;C. F. Morelli;P. Manitto;G. SperanzaUltimo
2009
Abstract
(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.
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