The meso trick

The meso trick
9 November 2008 - chemistry tricks

What: The meso trick. An organic synthesis for the preparation of a enantiopure compound from a meso starting compound (desymmetrization) .
Invented by: K. Laumen and M. Schneider in 1984 (DOI). In the original publication the meso compound is the diacetate of cis-3,5-dihydroxycyclopentene. The (R)-acetate group is selectively cleaved via biocatalysis by chymotrypsin to form the hydroxyacetate. The other enantiomer can then be obtained by a sequence of Tetrahydropyranyl protection and regular hydrolysis of the (S)-acetate group. Laumen and Schneider also coined the phrase meso-trick.

Invented by: Wang et al. also in 1984 (DOI). Used pig liver esterase on the same substrate getting them 80% enantiomeric excess.
Also see: the double meso-trick (DOI)
Recently invoked in: Oseltamivir total synthesis number 4 (DOI) and number 7 (DOI, also see previous post here)