title: A biocatalytic approach to synthesizing optically active orthogonally protected trans-cyclopentane-1,2-diamine derivatives.
abstract: A straightforward chemoenzymatic synthesis of optically active trans-N,N-dialkylcyclopentane-1,2-diamines has been efficiently developed starting out from their analogous (+/-)-trans-2-(N,N-dialkylamino)cyclopentanols. The route involves the one-pot stereospecific transformation of the racemic amino alcohols into racemic diamines and a subsequent kinetic resolution by means of lipase-B from Candida antarctica-catalyzed acylation reactions. The careful selection of both the alkyl substituents present in the diamine and the derivatization strategy applied to the enzymatic reaction enabled the easy preparation of other synthetically valuable optically active trans-cyclopentane-1,2-diamines derivatives.
authors.affiliation: Departamento de Química Orgánica e Inorgánica, Facultad de Química, Universidad de Oviedo, 33071-Oviedo, Spain.
authors.forename: Javier
authors.initials: J
authors.lastname: González-Sabín
authors.forename: Vicente
authors.initials: V
authors.lastname: Gotor
authors.forename: Francisca
authors.initials: F
authors.lastname: Rebolledo
mesh_terms: D002384:Catalysis; D003517:Cyclopentanes / Q000737:chemistry* / Q000378:metabolism*; D005656:Fungal Proteins; D008049:Lipase / Q000378:metabolism*; D015394:Molecular Structure
chemical_list: D003517:Cyclopentanes; D005656:Fungal Proteins; C467768:cyclopentane-1,2-diamine; D008049:Lipase; C431349:lipase B, Candida antarctica