90564-32-2Relevant academic research and scientific papers
Evaluation of a new protocol for enzymatic dynamic kinetic resolution of 3-hydroxy-3-(aryl)propanoic acids
Koszelewski, Dominik,Zysk, Malgorzata,Brodzka, Anna,Zadlo, Anna,Paprocki, Daniel,Ostaszewski, Ryszard
, p. 11014 - 11020 (2015/11/24)
The application of tandem metal-enzyme dynamic kinetic resolution (DKR) is a powerful tool for the manufacture of high-value chemical commodities. A new protocol of kinetic resolution based on irreversible enzymatic esterification of carboxylic acids with orthoesters was introduced to obtain optically active β-hydroxy esters. This procedure was combined with metal catalyzed racemization of the target substrate providing both (R) and (S) enantiomers of ethyl 3-hydroxy-3-(4-nitrophenyl)propanoate with a high yield of 89% at 40°C. A substantial influence of the enzyme type, organic co-solvent, and metal catalyst on the conversion and enantioselectivity of the enzymatic dynamic kinetic resolution was noted.
Choline chloride based eutectic solvents: Magical catalytic system for carbon-carbon bond formation in the rapid synthesis of β-hydroxy functionalized derivatives
Singh, Balvant Shyam,Lobo, Hyacintha Rennet,Shankarling, Ganapati Subray
experimental part, p. 70 - 74 (2012/07/17)
Significant β-hydroxy functionalized derivatives including nitroaldols, β-hydroxy nitriles and β-hydroxy carboxylic acids were successfully prepared, for the first time, by catalytic use of deep eutectic solvents (DES). This paper explores the versatility
Acetic acid aldol reactions in the presence of trimethylsilyl trifluoromethanesulfonate
Downey, C. Wade,Johnson, Miles W.,Lawrence, Daniel H.,Fleisher, Alan S.,Tracy, Kathryn J.
supporting information; experimental part, p. 5351 - 5354 (2010/10/20)
(Figure presented) In the presence of TMSOTf and a trialkylamine base, acetic acid undergoes aldol addition to non-enolizable aldehydes under exceptionally mild conditions. Acidic workup yields the β-hydroxy carboxylic acid. The reaction appears to procee
Asymmetric synthesis of both antipodes of β-hydroxy nitriles and β-Hydroxy carboxylic acids via enzymatic reduction or sequential reduction/hydrolysis
Ankati, Haribabu,Zhu, Dunming,Yang, Yan,Biehl, Edward R.,Hua, Ling
supporting information; experimental part, p. 1658 - 1662 (2009/08/08)
Use of isolated carbonyl reductases in the reduction of aromatic β-ketonitriles have completely eliminated the competing α-ethylation, which is often observed with whole cell biocatalysts. By choosing suitable recombinant carbonyl reductase, the reduction
Dirhodium(II) tetrakis[N-benzene-fused phthaloyl-(S)-piperidinonate] as a chiral lewis acid: Catalytic enantioselective aldol reactions of acetate-derived silylketene acetals and aldehydes
Washio, Takuya,Nakamura, Seiichi,Anada, Masahiro,Hashimoto, Shunichi
, p. 567 - 578 (2007/10/03)
A first example of chiral dirhodium(II) complex-catalyzed enantioselective Mukaiyama aldol reactions is described. The aldol addition reaction of methyl acetate-derived trimethylsilylketene acetal with specific aldehydes such as benzyloxyacetaldehyde and electron-poor aromatic aldehydes is effectively catalyzed by dirhodium(II) tetrakis[N-benzene-fused phthaloyl-(S)-piperidinonate] (1a), providing silylated aldol adducts in up to 94% ee.
Hetero Diels-Alder reaction involving (E)-3-(tert-butyldimethylsiloxy)-1-(2',3',4',6'-tetra-O-acetyl -β-D-gl ucopyranosyloxy)buta-1,3-diene and p-nitrobenzaldehyde
Lowe,Stoodley
, p. 6351 - 6354 (2007/10/02)
The title reaction, when carried out in carbon tetrachloride in the presence of a catalytic amount of Eu(fod)3, leads mainly to the cis-cycloadduct 6a; the product undergoes isomerisation to its epimer 7a in the presence of the catalyst in dich
