An efficient process for the resolution of cis-4-O-protected-2-cyclopenten-1,4-diol using pancreatin lipase in [C₈mim][PF₆] as a reusable system

Abstract

An efficient porcine pancreatin lipase-catalyzed transesterification of cis-4-O-TBS-2-cyclopenten-1,4-diol has been demonstrated in 1-octyl-3-methylimidazolium hexafluorophosphate, [C₈mim][PF₆] ionic liquid, furnishing both the alcohol and the corresponding acetate in excellent enantiomeric purity and yields. This typical reaction system containing the suspension of enzymes in ionic liquid medium could be reused up to five times to prepare the required products in consistent yields and ee's. The corresponding optically active derivatives are very useful intermediates towards the synthesis of various types of compounds, including prostanoids.