Reduction by a model of NAD(P)H. 33. Steric and electronic effects on asymmetric reduction of 2-acylpyridines.

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概要

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• Series of alkyl and fluorinated alkyl 2-pyridinyl ketones have been reduced by a chiral NAD(P)H-model (Me<SUB>2</SUB>PNPH) in the presence of magnesium ion in acetonitrile. Optical yield decreases in the order of substituent: CH<SUB>3</SUB>>C<SUB>2</SUB>H<SUB>5</SUB>>C(CH<SUB>3</SUB>)<SUB>3</SUB>>CH(CH<SUB>3</SUB>)<SUB>2</SUB> and CH<SUB>3</SUB>>CH<SUB>2</SUB>F>CHF<SUB>2</SUB>>CF<SUB>3</SUB>. The results have been interpreted in terms of conformation of the substrates for alkyl 2-pyridinyl ketones and of electronic competitional effect between two substituents for fluorinated alkyl 2-pyridinyl ketones. Magnesium ion freezes intermolecular arrangement at the transition state of the reduction.

• 公益社団法人 日本化学会の論文

著者

• Nakai Jun-ichi

  Institute for Chemical Research, Kyoto University

関連論文

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• Reduction by a model of NAD(P)H. 33. Steric and electronic effects on asymmetric reduction of 2-acylpyridines.

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