Autocatalytic Asymmetric Reduction of 2,6-Diacetylpyridine

Article abstract of DOI:10.1021/ol035515k

(Formula presented). We report here that the C₂-symmetric diol 2,6-bis(1-hydroxyethyl)pyridine (2) can effect chiral-catalyzed reduction of 2,6-diacetylpyridine (1) and produce more of the diol (2) with the same configuration in an enantiomerically enriched form. The two carbonyl functionalities of (1) are reduced in 90% conversion to produce the enantio-enriched C₂-symmetric diol (40% ee, 47% de) using zinc trifluoromethanesulfonate and a catalytic amount of the chiral C ₂-symmetric diol (2).