1491151-37-1Relevant articles and documents
Enzymatic transesterification of pharmacologically interesting β-aminocycloalkanol precursors
Gonzalez-Sabin, Javier,Rios-Lombardia, Nicolas,Gotor, Vicente,Moris, Francisco
, p. 1421 - 1425 (2013/12/04)
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.