Kinetic resolution of (±)-trans-and (±)-cis-2-phenylcyclopentanamine by CALB-catalyzed aminolysis of esters: the key role of the leaving group

J González-Sabı́n, V Gotor, F Rebolledo

Index: Gonzalez-Sabin, Javier; Gotor, Vicente; Rebolledo, Francisca Tetrahedron Asymmetry, 2004 , vol. 15, # 3 p. 481 - 488

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Citation Number: 33

Abstract

Kinetic resolution of (±)-trans-and (±)-cis-2-phenylcyclopentanamine is effectively performed by lipase B from Candida antarctica,(CALB)-catalyzed aminolysis reaction. Whereas reaction between (±)-trans-2-phenylcyclopentanamine and ethyl acetate proceeds with a very high E value (> 200) and conversion (50%), the corresponding acetylation of (±)-cis-2- phenylcyclopentanamine happens with low E value (16) and conversion (28%). ...