Chemoenzymatic preparation of optically active anthracene derivatives

摘要

Syntheses and lipase-catalyzed resolutions of a trans-2-aminocyclopentanol rac-2 and trans-cyclopentane-1,2-diamine rac-3, bearers of an anthracene unit, have been effectively carried out. Burkholderia cepacia lipase catalyzed the transesterification of the P-amino alcohol with very high enantioselectivity (E > 200). Lipase B from Candida antarctica showed moderate enantioselectivity in the acetylation of the diamine when 1-phenylethyl acetate was used as an acyl donor. In addition, the treatment of the optically active diamine (1S,2S)-3 (ee = 95%) with pyridine-2,6-dicarbonyl dichloride yielded the bis(aminoamide) 6, which was tested as a chiral solvating agent (CSA) of carboxylic acids. (C) 2008 Elsevier Ltd. All rights reserved.