engleski

Ferrocene Compounds. XXXVI. Lipase-catalyzed Enantioselective Acetylation of Prochiral 2-(omega-Ferrocenylalkyl)propane-1, 3-diols

Enantioselective acetylation (desymmetrization) of prochiral 2-(ferrocenylmethyl)propane-1, 2-diol (1), 2-(2-ferrocenylethyl)propane-1, 2-diol (2) and 2-(3-ferrocenylpropyl)propane-1, 2-diol (3) into chiral monoacetates [(+)-4-(+)-6], with a series of microbial lipases in benzene at 27_oC, revealed the lipase from Pseudomonas sp (PSL) as the most selective. Acetylation was fastest and the most enentioselective for conversion 1 to (+)-4 by PSL (97% e.e.). By comparison of the compounds (+)-4-(+)-6 with their benzene analogues of the known (R) absolute configuration, on the basis of their elution orders on Chiracel OD, and the same direction of their optical rotations, an R-configuration is proposed for (+)-monoacetates 4-6.

ferrocene prochiral diols; biocatalysis; enentioselectivity; lipases

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