93673-13-3Relevant academic research and scientific papers
Integrated Experimental and Computational Studies on the Organocatalytic Kinetic Resolution of β-Unfunctionalized Primary Alcohols Using a Chiral 1,2-Diamine: The Importance of Noncovalent Interactions
Mori, Seiji,Ojima, Kohei,Oriyama, Takeshi,Sakai, Naoki
supporting information, p. 4468 - 4475 (2022/03/14)
The enantioselective kinetic resolution of β-unfunctionalized primary alcohols with benzoyl chloride was carried out in the presence of a catalytic amount of a novel chiral 1,2-diamine derived from (S)-proline. Several valuable chiral 2-substituted propan-1-ols were obtained with good enantioselectivities. Density functional theory calculations revealed that the noncovalent interaction, such as CH-πinteraction, is crucial for the enantioselectivity of the resolution. This study was conducted through an interplay between experiment and computation.
Highly Enantioselective Catalytic Kinetic Resolution of α-Branched Aldehydes through Formal Cycloaddition with Homophthalic Anhydrides
Farid, Umar,Aiello, Maria Luisa,Connon, Stephen J.
supporting information, p. 10074 - 10079 (2019/07/18)
A new catalytic methodology was developed to promote an efficient one-pot kinetic resolution of racemic aldehydes with selectivity (s*) of up to 91 (99:1 d.r., >99 % ee) in a cycloaddition reaction with enolizable anhydrides to afford dihydroisocoumarin products (a core prevalent in natural products and molecules of medicinal interest) containing three contiguous stereocentres.
Easily accessible TADDOL-derived bisphosphonite ligands: Synthesis and application in the asymmetric hydroformylation of vinylarenes
Allmendinger, Simon,Kinuta, Hirotaka,Breit, Bernhard
supporting information, p. 41 - 45 (2015/03/03)
The synthesis of chiral bidentate bisphosphonite ligands based on the TADDOL motif from readily available starting materials has been developed. Taking advantage of the modular nature of the building blocks, a diverse ligand library has been prepared. Their catalytic potential has been evaluated in the asymmetric hydroformylation of styrene and derivatives. These catalysts showed high activity and provided the aldehydes in high enantiomeric purity.
Probing the parallel kinetic resolution of 1-phenylethanol using quasi-enantiomeric oxazolidinone adducts
Coulbeck, Elliot,Eames, Jason
, p. 2313 - 2325 (2008/03/18)
The parallel kinetic resolution of racemic 1-phenylethanol using an equimolar combination of quasi-enantiomeric oxazolidinones is discussed. The levels of diastereoselectivity were high leading to separable quasi-enantiomeric esters in good yield.
Chemoenzymatic synthesis of antiinflammatory drugs in enantiomerically pure form
Basak, Amit,Nag, Ahindra,Bhattacharya, Gautam,Mandal, Subrata,Nag, Sikha
, p. 2403 - 2407 (2007/10/03)
A novel chemoenzymatic route to chiral antiinflammatory drugs in enantiomerically pure form is described. Copyright (C) 2000 Elsevier Science Ltd.
Regio- and stereoselective hydrogenolysis of optically active diols via transfer hydrogenation : Synthesis of α- arylpropionic acids
Nandanan,Jayachandran,Phukan, Prodeep,Pais, Godwin C. G.,Sudalai
, p. 1221 - 1227 (2007/10/03)
Asymmetric synthesis of α-arylpropionic acids, Ibuprofen 1b, Naproxen 1c, and Flurbiprofen 1d have been achieved by employing Sharpless asymmetric dihydroxylation followed by the stereoselective hydrogenolysis of the chiral diols coupled with Jones' oxidation as the key steps. The regio- and stereoselective hydrogenolysis of the chiral diols at the benzylic position proceeds with retention of configuration for all the substrates studied.
DIFFERENCES IN REACTIVITY AND ENANTIOSELECTIVITY IN LIPASE REACTIONS WITH CARBOXYLIC ESTERS AND ALCOHOLS BEARING THE SAME STEREOGENIC CENTER
Sih, John C.,Gu, Rui Lin
, p. 357 - 360 (2007/10/02)
The reaction rate and stereochemical outcome of lipase reactions obtained with carboxylic esters and alcohols, which contain the same stereogenic center, can be modulated by changing the mode of the lipase reaction, i.e. ester hydrolysis versus alcohol acetylation.
Synthesis and in solution behaviour of new 2-substituted-4-thiazolidinecarboxylic acid derivatives
Chiarino,Ferrario,Pellacini,Sala
, p. 589 - 593 (2007/10/02)
A number of 2-substituted-4-thiazolidinecarboxylic acid derivatives were synthesized by cyclocondensation of L-cysteine or its esters with various aldehydes, resulting from acids provided with antiinflammatory properties. In the cyclocondensation a new chiral center at C-2 position of thiazolidine ring is formed giving rise to a mixture of diastereoisomers which can be partially separated. These diastereoisomers show in solution a fast epimerisation at the same chiral center as evidenced by 1H-nmr studies.
