3481-15-0Relevant academic research and scientific papers
Regeneration of NAD(P)H Using Glucose 6-Sulfate and Glucose-6-phosphate Dehydrogenase
Wong, Chi-Huey,Gordon, Jennifer,Cooney, Charles L.,Whitesides, George M.
, p. 4676 - 4679 (1981)
Glucose 6-sulfate and glucose-6-phosphate dehydrogenase have been used for NAD(P)H cofactor regeneration in preparations of (S)-benzyl-α-d1 alcohol and threo-DS(+)-isocitrate (0.1-mol scale).The reduced nicotinamide cofactors are mor
Reaction of alcohols (via the Mitsunobu reaction) and alkyl halides with chiral selone derivatizing agents
Wu, Ruilian,Odom, Jerome D.,Dunlap, R. Bruce,Silks III, Louis A.
, p. 1465 - 1470 (1999)
Coupling of a selone chiral derivatizing agent (CDA) to D,L-alkyl halides gives Se-alkylated adducts in yields ranging from 76-97%. Reaction of D,L-alcohols with the selone CDAs via the Mitsunobu reaction has given rise to Se-alkylated adducts in yields ranging from 82-92%. Examination of the 77Se NMR spectra of the resulting diastereomeric adducts indicates that discrimination of remotely disposed chiral centers is possible using this technique.
Method for synthesizing chiral deuterated primary alcohol
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Paragraph 0031-0036; 0160-0173, (2021/05/29)
The invention discloses a method for synthesizing chiral deuterated primary alcohol. The method comprises the following step: reacting an aldehyde compound in an aprotic organic solvent at room temperature under the action of a chiral cobalt catalyst by t
Controlling Selectivity in the Synthesis of Z-α,β-Unsaturated Amidines by Tuning the N-Sulfonyl Group in a Rhodium(II) Catalyzed 1,2-H Shift
Boyer, Alistair,Martin, Matthew L.
supporting information, p. 5857 - 5861 (2021/11/27)
N2-Sulfonyl-α-diazo amidines can be synthesized by the reaction of electron rich alkynyl amines with electron poor sulfonyl azides through 1,3-dipolar cycloaddition that proceeds with perfect regioselectivity. In the presence of rhodium(II) carboxylate catalysts, denitrogenation occurs to give the corresponding metallocarbene but there are then two competing processes: 1,2–H shift and O-transfer from the sulfonyl group to the metallocarbene center. The outcome can be controlled using an electron poor nitrobenzenesulfonyl group and large carboxylate rhodium ligands to select for 1,2–H shift, forming α,β-unsaturated amidines in high yield and with excellent Z-selectivity.
Imidazopyrazinone compound as well as preparation method and application thereof
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Paragraph 0070; 0074-0076, (2021/10/11)
The invention provides an imidazopyrazinone compound as well as a preparation method and application thereof. The imidazopyrazinone compound structure has the structure shown I, and R. 1 Is phenyl. R2 In the benzyl group, and the compound has at least one D substituent, the D substituent is at R. 1 And/or R2 . The compound has excellent luminescence performance, can be used as a substrate of NanoLuc luminescent system, and is applied to detection and drug detection of luciferase.
An Iron-Mesoionic Carbene Complex for Catalytic Intramolecular C-H Amination Utilizing Organic Azides
Albrecht, Martin,Keilwerth, Martin,Meyer, Karsten,Pividori, Daniel M.,Stroek, Wowa
supporting information, p. 20157 - 20165 (2021/12/09)
The synthesis of N-heterocycles is of paramount importance for the pharmaceutical industry. They are often synthesized through atom economic and environmentally unfriendly methods, generating significant waste. A less explored, but greener, alternative is
Aryl-Nickel-Catalyzed Benzylic Dehydrogenation of Electron-Deficient Heteroarenes
Zhang, Pengpeng,Huang, David,Newhouse, Timothy R.
supporting information, p. 1757 - 1762 (2020/02/04)
This manuscript describes the first practical benzylic dehydrogenation of electron-deficient heteroarenes, including pyridines, pyrazines, pyrimidines, pyridazines, and triazines. This transformation allows for the efficient benzylic oxidation of heteroarenes to afford heterocyclic styrenes by the action of nickel catalysis paired with an unconventional bromothiophene oxidant.
Frustrated Lewis pairs: A real alternative to deuteride/tritide reductions
Doubková, Sabina,Marek, Ale?
, p. 729 - 742 (2019/07/10)
Deuterium- and tritium-labeled compounds play a principal role in tracing of biologically active molecules in complicated biochemical systems. The state-of-the-art techniques using noble metal catalysts or strong reducing agents often suffers from low fun
Catalytic C-H Amination Mediated by Dipyrrin Cobalt Imidos
Baek, Yunjung,Betley, Theodore A.
supporting information, p. 7797 - 7806 (2019/05/22)
Reduction of (ArL)CoIIBr (ArL = 5-mesityl-1,9-(2,4,6-Ph3C6H2)dipyrrin) with potassium graphite afforded the novel CoI synthon (ArL)CoI. Treatment of (ArL)CoI with a stoichiometric amount of various alkyl azides (N3R) furnished three-coordinate CoIII alkyl imidos (ArL)Co(NR), as confirmed by single-crystal X-ray diffraction (R: CMe2Bu, CMe2(CH2)2CHMe2). The exclusive formation of four-coordinate cobalt tetrazido complexes (ArL)Co(κ2-N4R2) was observed upon addition of excess azide, inhibiting any subsequent C-H amination. However, when a weak C-H bond is appended to the imido moiety, as in the case of (4-azido-4-methylpentyl)benzene, intramolecular C-H amination kinetically outcompetes formation of the corresponding tetrazene species to generate 2,2-dimethyl-5-phenylpyrrolidine in a catalytic fashion without requiring product sequestration. The imido (ArL)Co(NAd) exists in equilibrium in the presence of pyridine with a four-coordinate cobalt imido (ArL)Co(NAd)(py) (Ka = 8.04 M-1), as determined by 1H NMR titration experiments. Kinetic studies revealed that pyridine binding slows down the formation of the tetrazido complex by blocking azide coordination to the CoIII imido. Further, (ArL)Co(NR)(py) displays enhanced C-H amination reactivity compared to that of the pyridine-free complex, enabling higher catalytic turnover numbers under milder conditions. The mechanism of C-H amination was probed via kinetic isotope effect experiments [kH/kD = 10.2(9)] and initial rate analysis with para-substituted azides, suggesting a two-step radical pathway. Lastly, the enhanced reactivity of (ArL)Co(NR)(py) can be correlated to a higher spin-state population, resulting in a decreased crystal field due to a geometry change upon pyridine coordination.
Asymmetric Catalysis Using Aromatic Aldehydes as Chiral α-Alkoxyalkyl Anions
Yabushita, Kenya,Yuasa, Akihiro,Nagao, Kazunori,Ohmiya, Hirohisa
, p. 113 - 117 (2019/01/08)
We have developed a new umpolung strategy for catalytically forming a chiral α-alkoxyalkyl anion from an aromatic aldehyde for use in asymmetric synthesis. The reaction between aromatic aldehydes and aryl or allyl electrophiles with a silylboronate utilizing a chiral copper-N-heterocyclic carbene catalyst and a palladium-bisphosphine catalyst in a synergistic manner occurred with high enantioselectivities to deliver the three-component coupling products, chiral silyl-protected secondary alcohol derivatives. Our method features the catalytic generation of enantioenriched chiral α-alkoxyalkylcopper(I) intermediates from aldehydes and their subsequent palladium-catalyzed stereospecific cross-coupling.
