Lipase catalyzed resolution of trans-11,12-bis(hydroxymethyl)-9,10-dihydro-9,10-ethanoanthracene: facile access to both enantiomers and the synthesis of their amino derivatives

The lipase mediated resolution of roof shaped trans-11,12-bis(hydroxymethyl)-9,10-dihydro-9,10-ethanoanthracene using vinyl acetate as an acetylating reagent is achieved. This method gives easy access to both enantiomers of the molecule in very high enantiomeric purity. The chiral diol is converted to diamino and aminoalcohol derivatives by simple chemical transformations.

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trans-11,12-Bis(hydroxymethyl)-9,10-dihydro-9,10-ethanoanthraceneC18H18O2[α]D = +11.0 (c 0.9, MeOH)Source of chirality: kinetic resolutionAbsolute configuration: (S,S)

trans-9,10-Dihydro-9,10-ethanoanthracene-11-acetoxymethyl-12-methanolC20H20O3[α]D = −14.1 (c 0.9, MeOH)Source of chirality: kinetic resolutionAbsolute configuration: (R,R)

trans-9,10-Dihydro-9,10-ethanoanthracene-11,12-bis-p-toluenesifonateC32H30O6S2[α]D = +28.1 (c 1.0, CHCl3)Source of chirality: kinetic resolutionAbsolute configuration: (S,S)

trans-9,10-Dihydro-9,10-ethanoanthracene-11-acetoxymethyl-12-p-toluenesulfonateC27H26O5S[α]D = −14.5 (c 1.0, CHCl3)Source of chirality: kinetic resolutionAbsolute configuration: (R,R)

trans-11,12-Bis(morpholine)-9,10-dihydro-9,10-ethanoanthraceneC26H32O2N2[α]D = +6.8 (c 0.9, CHCl3)Source of chirality: kinetic resolutionAbsolute configuration: (S,S)

trans-11,12-Bis(piperidine)-9,10-dihydro-9,10-ethanoanthraceneC28H36N2[α]D = +20.6 (c 1.0, CHCl3)Source of chirality: kinetic resolutionAbsolute configuration: (S,S)

trans-11,12-Bis(methylpiperazine)-9,10-dihydro-9,10-ethanoanthraceneC28H38N4[α]D = +18.7 (c 1.0, CHCl3)Source of chirality: kinetic resolutionAbsolute configuration: (S,S)

trans-11,12-Bis(pyrolidine)-9,10-dihydro-9,10-ethanoanthraceneC26H32N2[α]D = −49.9 (c 0.8, CHCl3)Source of chirality: kinetic resolutionAbsolute configuration: (R,R)