A biocatalytic approach to synthesizing optically active orthogonally protected trans-cyclopentane-1,2-diamine derivatives.
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.
González-Sabín
Javier
J
Departamento de Química Orgánica e Inorgánica, Facultad de Química, Universidad de Oviedo, 33071-Oviedo, Spain.
Gotor
Vicente
V
Rebolledo
Francisca
F
D002384:Catalysis; D003517:Cyclopentanes / Q000737:chemistry* / Q000378:metabolism*; D005656:Fungal Proteins; D008049:Lipase / Q000378:metabolism*; D015394:Molecular Structure
D003517:Cyclopentanes; D005656:Fungal Proteins; C467768:cyclopentane-1,2-diamine; D008049:Lipase; C431349:lipase B, Candida antarctica