Homochiral NADH models in the pyrrolo[2,3-b]pyridine series bearing one or two chiral auxiliaries. Asymmetric reduction of methyl benzoylformate and N-acetyl-enamines. Influence of the magnesium salt concentration on the asymmetric induction of reductions

Tetrahedron Asymmetry

Volumn 8, Issue 19, 1997, Pages 3309-3318

  Leroy, Corine ^a   Levacher, Vincent ^a   Dupas, Georges ^a   Quéguiner, Guy ^a   Bourguignon, Jean ^a  

^a IRCOF   (France)

Author keywords

[No Author keywords available]

Indexed keywords

PYRROLO[2,3 B]PYRIDINE DERIVATIVE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE;

ARTICLE; CHIRALITY; COMPLEX FORMATION; DRUG STRUCTURE; DRUG SYNTHESIS; MODEL; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0030882123     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00436-9     Document Type: Article

References (16)

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4. Ohno, A.; Kimura, T.; Yamamoto, H.; Kim, S. G.; Oka, S.; Ohnishi, Y.; Bull. Chem. Soc. Japan 1977, 50, 1535. Ohno, T.; Yamamoto, H.; Okamoto, T.; Oka, S.; Oka, S.; Ohnishi, Y. Bull.; Chem. Soc. Japan 1977, 50, 2385. Hughes, M.; Prince, R. H.; J. Inorg. Nucl. Chem. 1978, 40, 703.
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6. Bédat, J.; Plé, N.; Dupas, G.; Bourguignon, J.; Quéguiner G.; Tetrahedron: Asymmetry 1995, 6, 923. Kanomata et al. have recently reported a novel NADH model bearing a chiral amide group at C-3 derived from (S)-valinol and an oligomethylene chain bridging the 2-and 5-position of dihydropyridine ring short enough to generate a chirality plane. Methyl benzoylformate was reduced in high e.e. According to these authors the sense of asymmetric induction would be gouverned by the absolute structure of the solid parapyridinophane moiety which behave as an 'enzyme wall'. The amide moiety derived from an aminoalcohol would play the role of a 'tight chelating group' through the complexation of the magnesium ion with both carbonyl amide and alcohol function stabilizing the ternary complex. See: Kanomata, N.; Nakata, T.; Angew. Chem. Int. Ed. Engl. 1997, 36, 1207.
7. Bédat, J.; Plé, N.; Dupas, G.; Bourguignon, J.; Quéguiner G.; Tetrahedron: Asymmetry 1995, 6, 923. Kanomata et al. have recently reported a novel NADH model bearing a chiral amide group at C-3 derived from (S)-valinol and an oligomethylene chain bridging the 2-and 5-position of dihydropyridine ring short enough to generate a chirality plane. Methyl benzoylformate was reduced in high e.e. According to these authors the sense of asymmetric induction would be gouverned by the absolute structure of the solid parapyridinophane moiety which behave as an 'enzyme wall'. The amide moiety derived from an aminoalcohol would play the role of a 'tight chelating group' through the complexation of the magnesium ion with both carbonyl amide and alcohol function stabilizing the ternary complex. See: Kanomata, N.; Nakata, T.; Angew. Chem. Int. Ed. Engl. 1997, 36, 1207.
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15. 5
16. Leroy, C.; Dupas, G.; Bourguignon, J.; Quéguiner, G.; Tetrahedron 1994, 50, 13135.