Lipase–triethylamine-mediated dynamic transesterification of a tricyclic acyloin having a latent meso-structure: a new route to optically pure oxodicyclopentadiene
- 1 January 1997
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Chemical Communications
- No. 15,p. 1399-1400
- https://doi.org/10.1039/a702910a
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.Keywords
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