A route to enantiomerically pure 5-(2′-hydroxyethyl)cyclopent-2-en-1-ol and its absolute configuration by Mosher esters

The (±)-5-(2′-hydroxyethyl)cyclopent-2-en-1-ol 1 was prepared in a one-pot procedure, and was resolved using lipase AK and vinyl acetate with high ee. This provides a readily available chiral synthon for the synthesis of a wide variety of biologically interesting molecules. Further, the absolute configuration of diol 1 was confirmed directly by the Mosher ester method.

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(1S,5R)-(−)-5-(2′-Hydroxyethyl)cyclopent-2-en-olC7H12O2[α]D20=-90.2 (c 0.006, CHCl3)Absolute configuration: (1S,5R)Source of chirality: Enzymatic Kinetic Resolution