Enantio-Differentiating Hydrogenation of Methyl 2-Furoylacetate and Its Analogs over Tartaric Acid-Modified Raney Nickel.

Hydrogenation of methyl 2-furoylacetate over TA-MRNi reduced the three unsaturated bonds to give methyl tetrahydro-2-furoylacetate, the enantiomeric excess tee) of which at the 3-position was 77%, whereas the 4-position was racemic. Under the same conditions, the substrate of 4-methoxycarbonyl analogue was resulted in hydrogenation of only the ketone moiety to give the corresponding chiral sec-alcohol having a furan ring in 69% ee.