Stereoselectivity of the Enzymatic Reduction of Aldehydic and Ketonic Carbonyl Groups in Planar Chiral Organomanganese Complexes(Organic Chemistry)

概要

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(±)-Tricarbonyl(η^5-1-formyl-2-methylcyclopentadienyl)manganese (1) was optically resolved with horse liver alcohol dehydrogenase (HLADH) and two species of yeasts, Saccharomyces sp. H-1 and Rhodotorula rubra IFO 889. Usually, (1R)-1 was preferentially reduced to give (-)-alcohol 2 of ≥97% e.e.-84% e.e. Ketone analogue (±)-tricarbonyl(η^5-1-acetyl-2-methylcyclopentadienyl)-manganese (4) was reduced by the yeasts. The major product by S. sp. H-1 was the (1S,2R,1'S)-(+)-alcohol (5) (≥98% e.e.) and the minor product, the (1R,25,1'S)-(-)-alcohol (6) (86% e.e.). R. rubra gave only the latter alcohol (≥99% e.e.). The stereodifferentiation mechanism for these bioreductions is discussed in terms of the Prelog rule. The mechanism for HLADH reduction was examined with computer graphics.
社団法人日本農芸化学会の論文
1990-07-23