1107635-42-6Relevant academic research and scientific papers
Lewis Base–Br?nsted Acid–Enzyme Catalysis in Enantioselective Multistep One-Pot Syntheses
Giesler, Markus,Guder, Marian,Hartmann, Laura,Mantel, Marvin,Pietruszka, J?rg,Rüthlein, Elisabeth
supporting information, p. 16700 - 16706 (2021/05/07)
Establishing one-pot, multi-step protocols combining different types of catalysts is one important goal for increasing efficiency in modern organic synthesis. In particular, the high potential of biocatalysts still needs to be harvested. Based on an in-depth mechanistic investigation of a new organocatalytic protocol employing two catalysts {1,4-diazabicyclo[2.2.2]octane (DABCO); benzoic acid (BzOH)}, a sequence was established providing starting materials for enzymatic refinement (ene reductase; alcohol dehydrogenase): A gram-scale access to a variety of enantiopure key building blocks for natural product syntheses was enabled utilizing up to six catalytic steps within the same reaction vessel.
METHODS AND COMPOUNDS FOR RESTORING MUTANT p53 FUNCTION
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, (2022/01/06)
Mutations in oncogenes and tumor suppressors contribute to the development and progression of cancer. The present disclosure describes compounds and methods that restore DNA binding affinity of p53 mutants. The compounds of the present disclosure can bind to mutant p53 and restore the ability of the p53 mutant to bind DNA and activate downstream effectors involved in tumor suppression. The disclosed compounds can be used to reduce the progression of cancers that contain a p53 mutation.
Simple organocatalysts in multi-step reactions: An efficient one-pot Morita-Baylis-Hillman-type α-hydroxymethylation of vinyl ketones followed by the convenient, temperature-controlled one-pot etherification using alcohols
Mantel, Marvin,Guder, Marian,Pietruszka, J?rg
supporting information, p. 5442 - 5450 (2018/05/25)
1,4-Diazabicyclo[2.2.2]octane (DABCO) was utilized as versatile catalyst in a one-pot synthesis: First, for the preparation of alcoholic formaldehyde solutions from para-formaldehyde catalysed by using low loadings of inexpensive DABCO. Second, for the fast α-hydroxymethylation of alkylic and aromatic vinyl ketones in high yields. In a third step, the same catalyst can be used for an optional, temperature controlled in situ etherification of the Morita-Baylis-Hillman product with various alcohols on a multi-gram scale in moderate to good overall yields and high purities. Furthermore, an application of the ether in the enantioselective synthesis of a common building block for total synthesis is shown, thus providing a gram-scale access from inexpensive bulk chemicals.
Concise synthesis of α-(hydroxymethyl) alkyl and aryl vinyl ketones
Kraem, Jihene Ben,Amri, Hassen
, p. 110 - 117 (2012/10/30)
2,4-Diketoesters 2 have first been reported as starting materials for the synthesis of a new class of α-hydroxymethyl-α,β-unsaturated ketones 3. Thus, under heterogeneous liquid-liquid medium in the presence of concentrated aqueous potassium carbonate as a base, both aliphatic and aromatic 2,4-dioxoalkanoates 2 react with aqueous formaldehyde to afford the corresponding ketones 3 in fair to good yields. Copyright Taylor & Francis Group, LLC.
A Synthetic and Computational Investigation into the Direct Synthesis of α -Hydroxymethylated Enones from β-keto Phosphonates
Ryan, Sarah J.,Thompson, Christopher D.,Lupton, David W.
experimental part, p. 720 - 727 (2010/02/16)
The synthesis of a range of -hydroxymethylated enones has been achieved using the Villiras modification of the HornerWadsworthEmmons (HWE) reaction. Scope, limitations, and mechanistic aspects of this reaction were investigated using a combination of synthetic and computational studies. These investigations support a SchlosserCorey type reaction mechanism that is balanced between two pathways with the outcome influenced by the steric environment of the substrate. CSIRO 2009.
Facile 1,3-diaza-Claisen rearrangements of tertiary allylic amines bearing an electron-deficient alkene
Aranha, Rachel M.,Bowser, Amy M.,Madalengoitia, Jose S.
supporting information; experimental part, p. 575 - 578 (2009/07/18)
(Chemical Equation Presented) Tertiary allylic amines with an electron-deficient alkene react with isocyanates and isothiocyanates to give highly substituted ureas and thioureas arising from formal 1,3-diaza-Claisen rearrangements. Isocyanates and isothiocyanates with strong electron-withdrawing groups are more reactive. Similarly, the data suggest that a stronger electron-withdrawing substituent on the alkene favors a faster reaction, but this may be offset by sterlcs in the cyclic transition state.
