6811-98-9Relevant academic research and scientific papers
Photoinduced Hydrocarboxylation via Thiol-Catalyzed Delivery of Formate across Activated Alkenes
Alektiar, Sara N.,Wickens, Zachary K.
supporting information, p. 13022 - 13028 (2021/09/03)
Herein we disclose a new photochemical process to prepare carboxylic acids from formate salts and alkenes. This redox-neutral hydrocarboxylation proceeds in high yields across diverse functionalized alkene substrates with excellent regioselectivity. This operationally simple procedure can be readily scaled in batch at low photocatalyst loading (0.01% photocatalyst). Furthermore, this new reaction can leverage commercially available formate carbon isotologues to enable the direct synthesis of isotopically labeled carboxylic acids. Mechanistic studies support the working model involving a thiol-catalyzed radical chain process wherein the atoms from formate are delivered across the alkene substrate via CO2?- as a key reactive intermediate.
Direct β-Selective Hydrocarboxylation of Styrenes with CO2 Enabled by Continuous Flow Photoredox Catalysis
Seo, Hyowon,Liu, Aofei,Jamison, Timothy F.
supporting information, p. 13969 - 13972 (2017/10/17)
The direct β-selective hydrocarboxylation of styrenes under atmospheric pressure of CO2 has been developed using photoredox catalysis in continuous flow. The scope of this methodology was demonstrated with a range of functionalized terminal styrenes, as well as α-substituted and β-substituted styrenes.
Regioselective hydroformylation of allylic alcohols
Lightburn, Thomas E.,De Paolis, Omar A.,Cheng, Ka H.,Tan, Kian L.
supporting information; experimental part, p. 2686 - 2689 (2011/06/28)
A highly regioselective hydroformylation of allylic alcohols is reported toward the synthesis of β-hydroxy-acid and aldehyde products. The selectivity is achieved through the use of a ligand that reversibly binds to alcohols in situ, allowing for a directed hydroformylation to occur. The application to trisubstituted olefins was also demonstrated, which yields a single diastereomer product consistent with a stereospecific addition of CO and hydrogen.
Selective reductions of cyclic 1,3-diesters by using SmI2 and H2O
Collins, Karl D.,Oliveira, Juliana M.,Guazzelli, Giuditta,Sautier, Brice,De Grazia, Sara,Matsubara, Hiroshi,Helliwell, Madeleine,Procter, David J.
scheme or table, p. 10240 - 10249 (2010/11/18)
SmI2/H2O reduces cyclic 1,3-diesters to 3-hydroxyacids with no over reduction. Furthermore, the reagent system is selective for cyclic 1,3-diesters over acyclic 1,3-diesters, and esters. Radicals formed by one-electron reduction of the ester carbonyl group have been exploited in intramolecular additions to alkenes. The ketal unit and the reaction temperature have a marked impact on the diastereoselectivity of the cyclizations. Cyclization cascades are possible when two alkenes are present in the starting cyclic diester and lead to the formation of two rings and four stereocenters with excellent stereocontrol.
Method for producing optically active phenylpropionic acid derivative
-
Page column 7, (2008/06/13)
Optically active N-(S-2-acetylthiomethyl-1-oxo-3-phenylpropyl)-glycine benzyl ester useful as an enkephalin inhibitory agent or ACE inhibitory agent can be produced at low cost in an industrial manner, by a method comprising subjecting optically active 2-hydroxymethyl-3-phenylpropionic acid and glycine benzyl ester to condensation to subsequently convert the hydroxyl group into an elimination group, and substituting the elimination group with an acetylthio group.
Cleavage of β-lactone ring by serine protease. Mechanistic implications
Kim, Dong H.,Park, Jeong-il,Chung, Sang J.,Park, Jung Dae,Park, No-Kyung,Han, Jong Hoon
, p. 2553 - 2560 (2007/10/03)
Both enantiomers of 3-benzyl-2-oxetanone (1) were found to be slowly hydrolyzed substrates of α-chymotrypsin having kcat values of 0.134±0.008 and 0.105±0.004 min-1 for (R)-1 and (S)-1, respectively, revealing that α-CT is virtually unable to differentiate the enantiomers in the hydrolysis of 1. The initial step to form the acyl-enzyme intermediate by the attack of Ser-195 hydroxyl on the β-lactone ring at the 2-position in the hydrolysis reaction may not be enzymatically driven, but the relief of high ring strain energy of β-lactone may constitute a major driving force. The deacylation step is also attenuated, which is possibly due to the hydrogen bond that would be formed between the imidazole nitrogen of His-57 and the hydroxyl group generated during the acylation in the case of (R)-1, but in the α-CT catalyzed hydrolysis of (S)-1 the imidazole nitrogen may form a hydrogen bond with the ester carbonyl oxygen.
Process for producing propionic acid derivatives
-
, (2008/06/13)
A process for producing a 2-aralkyl-3-hydroxypropionic acid (or its ester), comprising the steps of: reacting a 3-hydroxy-2-methylene-3-arylpropionic acid ester, easily obtained by the reaction of an arylaldehyde with an acrylic acid ester, with an acid anhydride to form a 2-aralkylidene-3-acyloxypropionic acid ester; subjecting the same to hydrolysis or alcoholysis; and reducing the resulting 2-aralkylidene-3-hydroxypropionic acid or its ester. The reduction step may be conducted in the presence of a base.
Method for producing optically active phenylpropionic acid derivative
-
, (2011/05/18)
Optically active N-(S-2-acetylthiomethyl-1-oxo-3-phenylpropyl)-glycine benzyl ester useful as an enkephalin inhibitory agent or ACE inhibitory agent can be produced at low cost in an industrial manner, by a method comprising subjecting optically active 2-
Highly regioselective intramolecular hydroxymethylation of α,β-unsaturated carboxylic acids
Linker, Torsten,Maurer, Michael,Rebien, Frank
, p. 8363 - 8366 (2007/10/03)
A convenient synthesis of hydroxy esters 7 and lactones 8 by starting from easily available α,β-unsaturated carbocylic acids 4 is described. The key step of this transformation is a hitherto unknown radical cyclization of silyl esters, which exhibits a high degree of regioselectivity through steric and orbital control.
