Highly reactive and stereoselective (R)-and (S)-3-(N, N-dimethylcarbamoyl)-1, 2, 4-trimethyl-1, 4-dihydropyridines for NADH-NAD+ mimicry

…, PM Van Lier, JAJM Vekemans, HM Buck

Index: Kok, Peter M. T. de; Bastiaansen, Loek A. M.; Lier, Pieter M. van; Vekemans, Jozef A. J. M.; Buck, Henk M. Journal of Organic Chemistry, 1989 ,  vol. 54,  # 6  p. 1313 - 1320

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Citation Number: 75

Abstract

NADH model compound 3-(N~-dimethylcarbamoyl)-1, 2, 4-trimethyl-l, 4-dihydrop~ idine, 1, has been resolved into its enantiomers. Subsequently these hydride donors were brought into reaction with divergent carbonyl substrates, eg, methyl benzoylformate, methyl pyruvate, acetone-& and DDQ. Significant asymmetric induction was observed in the corresponding axially chiral NAD+ analogue 3-(N, N-dimethylcarbamoyl)-1, 2, 4-trimethyl-pyridinium ...