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Autocatalytic asymmetric reduction of 2,6-diacetylpyridine.

Org Lett. 2003 Oct 16;5(21):3947-9.

Autocatalytic asymmetric reduction of 2,6-diacetylpyridine.

Panosyan FB, Chin J.
Department of Chemistry, University of Toronto, 80 St. George Street,
M5S 3H6, Toronto, Canada.

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).
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