Chemoenzymatic preparation of optically active anthracene derivatives

Abstract

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 β-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 (1 S,2 S)- 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.