Chiral organometallic NADH mimics: stereoselective reduction of ethyl benzoylformate utilising the homochiral auxiliary [(η5-C5H5)Fe(CO)(PPh3)] at C-3 and a chiral β-hydroxy-carboxamide derived from valinol at C-5

Burgess, Vicky A.; Davies, Stephen G.; Skerlj, Renato T.

doi:10.1039/c39900001759

Cited by 18 publications

(5 citation statements)

References 14 publications

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“…Mostly, the latter procedure afforded the better yield (see Experimental Section). Complex 5 has been already reported by Davies et al1a,1b,1d Complexes 10 and 11 were obtained by using the (in situ prepared) mixed anhydride from pivalic acid and the monomethylester of pyridine‐2,6‐dicarboxylic acid.…”

Section: Resultsmentioning

confidence: 83%

Metalcarbonyl Complexes of Iron, Rhenium, and Manganese with 2‐, 3‐, or 4‐Pyridoyl (CO‐Pyridyl) Ligands

Weinrich

Beck

2014

Zeitschrift anorg allge chemie

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Section: Resultsmentioning

confidence: 83%

Metalcarbonyl Complexes of Iron, Rhenium, and Manganese with 2‐, 3‐, or 4‐Pyridoyl (CO‐Pyridyl) Ligands

Weinrich

Beck

2014

Zeitschrift anorg allge chemie

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“…Davies and co-workers prepared NAD(P)H models 12, 13, and 14 that possess a new chiral center at the side chain (Figure 9). [38][39][40] The homochiral complex model 12 reduced the substrate to (R)-ethylmandelate with 89% ee. Hydroxyl groups in 13 played a very important role (97% ee), allowing the chiral NAD(P)H model and magnesium ions to bind more closely in the transition state.…”

Section: Effect Of the Substituents Of Dihydronicotinamidementioning

confidence: 99%

“…Hydroxyl groups in 13 played a very important role (97% ee), allowing the chiral NAD(P)H model and magnesium ions to bind more closely in the transition state. [38][39][40] Sulfinyl groups have a mild electron-withdrawing character. Imanishi et al synthesized NAD(P)H model 15 possessing a sulfinyl group at the 3-position of the dihydropyridine ring (Scheme 2).…”

Section: Effect Of the Substituents Of Dihydronicotinamidementioning

confidence: 99%

Progress on Chiral NAD(P)H Model Compounds

Chen

Wang

Xing

et al. 2016

Synlett

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NAD(P)H and NAD + have a significant role in biochemistry, and many NAD(P)H models received particular attention. Research in NADH models mainly focuses on asymmetric reduction and life sciences. Over the past few decades, a particularly large number of new chiral NAD(P)H models have appeared, and there have been significant developments in this area. We summarized advanced research in chiral NAD(P)H models in this paper. These models not only show very good performance in asymmetric reduction, but also have excellent fluorescence features. In addition, we present a discussion about some recent studies on the asymmetric reduction of NAD(P)H-dependent dehydrogenase, and we open a new door on research into NAD(P)H models. At last, some advances focused on the fluorescence phenomenon of some chiral NAD(P)H models have also been summarized.

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“…Coenzyme NADH, a cofactor of l -lactate dehydrogenase, functions as an enantioselective agent that reduces pyruvate to l -lactate during anaerobic glycolysis. During the past several decades, efforts have been made to create model compounds mimicking the activity of the NAD + −NADH redox couple. − The introduction of an optically active N -substituent in the amide of 1-alkylated 1,4-dihydronicotinamides, e.g., 1 , can induce modest to moderate chirality transfer toward carbonyl compounds (Figure ). , Furthermore, Ohno and co-workers have improved considerably chirality transfer by the additional introduction of methyl groups at C2 and C4 in the NADH model, e.g., compound 2 . The new chiral center at C4 controls the mode of hydride transfer.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Properties, and NAD⁺-NADH-Type Redox Ability of 14-Substituted 1,3-Dimethyl-5,10-methanocycloundeca[4,5]pyrrolo[2,3-d]pyrimidine-2,4(1,3H)-dionylium Tetrafluoroborates and Their Hydride Adducts

et al. 2006

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A synthesis of 14-substituted 1,3-dimethyl-5,10-methanocycloundeca[4,5]pyrrolo[2,3-d]pyrimidine-2,4(1,3H)-dionylium tetrafluoroborates 11a,b(+).BF4- was accomplished by the methylation of 5,10-methanocycloundeca[4,5]pyrrolo[2,3-d]pyrimidine-2,4(1,3H)-dione derivatives with MeI and following anion-exchange reaction by treatment with 42% aq HBF(4). Compound 11b(+).BF4- was synthesized alternatively by the reaction of 1,6-methano[11]annulenylium tetrafluoroborate with 6-phenylamino-1,3-dimethyluracil and following oxidative cyclization reaction. Remarkable structural characteristics of 11a,b(+)were clarified on inspection of the UV-vis and NMR spectral data as well as X-ray crystal analyses. The stability of cations 11a,b(+)() is expressed by the pK(R+) values which were determined spectrophotometrically as 9.8 and 9.7, which are smaller by 1.4 and 1.2 pH units than those of the corresponding seven-membered ring cations, respectively; however, the values are larger by 3.6 and 3.5 pH units than that of the parent 1,6-methano[11]annulenylium ion (pK(R+) = 6.2). The feature is rationalized on the basis of the perturbation derived from the bond fixation of the parent cation and the electron-donating ability of pyrrolopyrimidine. The electrochemical reduction of 11a,b(+).BF4- exhibited reduction potential at -0.58 and -0.52 (V vs Ag/AgNO3) upon cyclic voltammetry (CV). Reaction of 11a(+).BF4- with hydride afforded mixures of the C13- and C11-adducts in a ratio with hydride afforded, on the other hand, the C13-adduct as a single product. In both cations, the methano-bridge seemed to control the nucleophilic attack to the C13 favorably with exo-selectivity. The photoinduced autorecycling oxidation reactions of 11a,b(+).BF4- toward some amines under aerobic conditions were carried out to give the corresponding imines (isolated by converting to the corresponding 2,4-dinitrophenylhydrazones) with the recycling number of 1.1 to 32.2. Furthermore, as an example of the NAD+-NADH models, the reduction of a pyruvate analogue and some carbonyl compounds with the hydride adducts of 11a,b+.BF4- was accomplished for the first time to give the corresponding alcohol derivatives.

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Chiral organometallic NADH mimics: stereoselective reduction of ethyl benzoylformate utilising the homochiral auxiliary [(η⁵-C₅H₅)Fe(CO)(PPh₃)] at C-3 and a chiral β-hydroxy-carboxamide derived from valinol at C-5

Cited by 18 publications

References 14 publications

Metalcarbonyl Complexes of Iron, Rhenium, and Manganese with 2‐, 3‐, or 4‐Pyridoyl (CO‐Pyridyl) Ligands

Metalcarbonyl Complexes of Iron, Rhenium, and Manganese with 2‐, 3‐, or 4‐Pyridoyl (CO‐Pyridyl) Ligands

Progress on Chiral NAD(P)H Model Compounds

Synthesis, Properties, and NAD⁺-NADH-Type Redox Ability of 14-Substituted 1,3-Dimethyl-5,10-methanocycloundeca[4,5]pyrrolo[2,3-d]pyrimidine-2,4(1,3H)-dionylium Tetrafluoroborates and Their Hydride Adducts

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Chiral organometallic NADH mimics: stereoselective reduction of ethyl benzoylformate utilising the homochiral auxiliary [(η5-C5H5)Fe(CO)(PPh3)] at C-3 and a chiral β-hydroxy-carboxamide derived from valinol at C-5

Cited by 18 publications

References 14 publications

Metalcarbonyl Complexes of Iron, Rhenium, and Manganese with 2‐, 3‐, or 4‐Pyridoyl (CO‐Pyridyl) Ligands

Metalcarbonyl Complexes of Iron, Rhenium, and Manganese with 2‐, 3‐, or 4‐Pyridoyl (CO‐Pyridyl) Ligands

Progress on Chiral NAD(P)H Model Compounds

Synthesis, Properties, and NAD+-NADH-Type Redox Ability of 14-Substituted 1,3-Dimethyl-5,10-methanocycloundeca[4,5]pyrrolo[2,3-d]pyrimidine-2,4(1,3H)-dionylium Tetrafluoroborates and Their Hydride Adducts

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Chiral organometallic NADH mimics: stereoselective reduction of ethyl benzoylformate utilising the homochiral auxiliary [(η⁵-C₅H₅)Fe(CO)(PPh₃)] at C-3 and a chiral β-hydroxy-carboxamide derived from valinol at C-5

Synthesis, Properties, and NAD⁺-NADH-Type Redox Ability of 14-Substituted 1,3-Dimethyl-5,10-methanocycloundeca[4,5]pyrrolo[2,3-d]pyrimidine-2,4(1,3H)-dionylium Tetrafluoroborates and Their Hydride Adducts