- Enzymatic transesterification of pharmacologically interesting β-aminocycloalkanol precursors
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Chemoenzymatic syntheses of both enantiomers of cis- and trans-2-aminocyclopentanol as well as cis- and trans-2-aminocyclohexanol, which are valuable building blocks for a plethora of ligands and pharmaceuticals have been efficiently carried out. The strategy involves the stereospecific syntheses of racemic aminocycloalkanol precursors via tagging of a phthalimide as a masking group and subsequent lipase-catalyzed kinetic resolution. Most of the lipases exhibited excellent enantioselectivity (E a‰ 200) in the transesterification reactions of trans-derivatives, with both N-protected (R,R)-amino acetates and (S,S)-amino alcohols being isolated in enantiopure form. With regard to cis-derivatives, lipases were also very selective, even though the biotransformations were significantly slower.
- Gonzalez-Sabin, Javier,Rios-Lombardia, Nicolas,Gotor, Vicente,Moris, Francisco
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p. 1421 - 1425
(2013/12/04)
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- Cyclic trans-β-amino alcohols: Preparation and enzymatic kinetic resolution
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Enantioenriched cyclic β-amino alcohols, trans-2-aminocyclohexanols (ee, >99%), trans-2-aminocyclopentanols (ee, >99%), trans-1-amino-2- indanols (ee, >99%) and trans-2-amino-1-indanols (ee, ~98%) were prepared in high yields via an Arthrobacter sp. Lipase/PLAP catalyzed kinetic resolution of racemic phthalimido acetates. The addition of toluene as a co-solvent dramatically improved the hydrolysis and enantioselectivity, whereas for indanols, substrate immobilization on Celite improved the efficacy of the kinetic resolution.
- Rouf, Abdul,Gupta, Pankaj,Aga, Mushtaq A.,Kumar, Brijesh,Parshad, Rajinder,Taneja, Subhash C.
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experimental part
p. 2134 - 2143
(2012/05/04)
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