Enzyme-catalysed kinetic resolution of N, O-diacetyl derivatives of cyclic 1,3-amino alcohols

Racemates of N, O-diacetyl derivatives of cis- and trans-2-aminomethylcyclopentanols 5 and 6 and cis- and trans-2-aminomethylcyclohexanols 7 and 8 were resolved through lipase-catalysed asymmetric O-deacylation at the (1 R) stereogenic centre. The gram-scale resolutions of 5– 8 were carried out with...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 2001-07, Vol.12 (13), p.1881-1886
Main Authors: Kámán, Judit, Forró, Enikő, Fülöp, Ferenc
Format: Article
Language:English
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Summary:Racemates of N, O-diacetyl derivatives of cis- and trans-2-aminomethylcyclopentanols 5 and 6 and cis- and trans-2-aminomethylcyclohexanols 7 and 8 were resolved through lipase-catalysed asymmetric O-deacylation at the (1 R) stereogenic centre. The gram-scale resolutions of 5– 8 were carried out with ethanol in di- iso-propyl ether in the presence of Novozym 435. The unreacted N, O-diacetyl compounds 5a– 8a were transformed to the corresponding alcohols 5c– 8c without loss of enantiopurity. N, O-Diacetyl derivatives of racemic cyclic 1,3-amino alcohols were resolved through lipase-catalysed asymmetric O-deacylation at the (1 R) stereogenic centre.
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(01)00318-4