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Updated: Jul 17, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
A biocatalytic approach to synthesizing optically active orthogonally protected trans-cyclopentane-1,2-diamine
Javier González-Sabín1, Vicente Gotor, Francisca Rebolledo
1Departamento de Química Orgánica e Inorgánica, Facultad de Química, Universidad de Oviedo, 33071-Oviedo, Spain.
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.
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