Autocatalytic asymmetric reduction of 2,6-diacetylpyridine.
[reaction: see text] We report here that the C(2)-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 C(2)-symmetric diol (40% ee, 47% de) using zinc trifluoromethanesulfonate and a catalytic amount of the chiral C(2)-symmetric diol (2).
Panosyan
Francis B
FB
Department of Chemistry, University of Toronto, 80 St. George Street, M5S 3H6, Toronto, Canada.
Chin
Jik
J