Biocatalytic approaches toward the synthesis of both enantiomers of trans-cyclopentane-1,2-diamine.
[reaction: see text] A lipase-catalyzed double monoaminolysis of dimethyl malonate by (+/-)-trans-cyclopentane-1,2-diamine allows the sequential resolution of the latter compound, affording an enantiopure bis(amidoester), which is subsequently transformed into an optically active polyamine. As an alternative, both enantiomers of the diamine can be obtained from enantiopure (+)- or (-)-2-aminocyclopentanol, prepared by enzymatic resolution.
Luna
Amparo
A
Departamento de Química Orgánica e Inorgánica, Facultad de Química, Universidad de Oviedo, 33071-Oviedo, Spain.
Alfonso
Ignacio
I
Gotor
Vicente
V
D000588:Amines / Q000138:chemical synthesis*; D002384:Catalysis; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000588:Amines; D003517:Cyclopentanes; C467768:cyclopentane-1,2-diamine