Lipase–triethylamine-mediated dynamic transesterification of a tricyclic acyloin having a latent meso-structure: a new route to optically pure oxodicyclopentadiene

Abstract

The racemic tricyclic acyloin (±)-endo-3-hydroxytricyclo[4.2.1.0 ^2,5 ]non-7-en -4-one has been dynamically resolved via the transient formation of the meso-enediol isomer under lipase–triethylamine-mediated kinetic transesterification conditions to give the single chiral acetate (-)-endo-3-acetoxytricyclo[4.2.1.0 ^2,5 ]non-7-en- 4-one, serving as a precursor of (-)-oxodicyclopentadiene, in excellent optical and chemical yields.