Reduction by a model of NAD(P)H. 32. Stereoselective reduction of camphoroquinone by a chiral NAD(P)H model.
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概要
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(+)-, (−)-, and racemic camphoroquinones (CQ) were reduced by each of four NAD(P)H-models such as <I>N</I>-(α-methylbenzyl)-1-propyl-2,4-dimethyl-1,4-dihydronicotinamide (Me<SUB>2</SUB>PNPH) in the presence of magnesium ion in acetonitrile with a view to elucidating the intermolecular arrangement in the transition state for asymmetric reduction. Partial rate factors for each attacking mode were calculated. Electronegative substituents in the substrate prefer to facing the carbamoyl group in Me<SUB>2</SUB>PNPH, which is the most important factor determining the stereochemical course of the reduction. 1-Methyl group in CQ has a tendency to interfere with the dihydropyridine moiety in Me<SUB>2</SUB>PNPH approaching the C<SUB>2</SUB>-carbonyl group in CQ. This interference is more important for the selectivity than the intrinsic <I>exo</I>/<I>endo</I> reactivity difference.
- 公益社団法人 日本化学会の論文
著者
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Ohno Atsuyoshi
Institute For Chemical Research Kyoto Univ.
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Oka Shinzaburo
Institute For Chemical Research Kyoto University
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Nakai Jun-ichi
Institute for Chemical Research, Kyoto University
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Goto Takehiko
Institute for Chemical Research, Kyoto University
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