Enantio-differentiating hydrogenation of methyl 2-furoylacetate and its analogs over tartaric acid-modified Raney nickel

Article abstract of DOI:10.1246/cl.1999.1055

Hydrogenation of methyl 2-furoylacetate over TA-MRNi reduced the three unsaturated bonds to give methyl tetrahydro-2-furoylacetate, the enantiomeric excess (ee) 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.