89867-54-9Relevant academic research and scientific papers
Facile and regioselective dealkylation of alkyl aryl ethers using niobium(V) pentachloride
Sudo, Yukinori,Arai, Shigeru,Nishida, Atsushi
, p. 752 - 758 (2006)
A simple and facile method for the cleavage of carbon-oxygen bonds promoted by niobium pentachloride(V) is described. Excellent yields and regioselectivities were observed with various alkyl aryl ethers to give the phenols. NMR studies revealed the formation of monoaryloxy niobium salt(V), and a neighboring-group effect may play a significant role in the regioselectivity. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
Photoracemization-Based Viedma Ripening of a BINOL Derivative
Belletti, Giuseppe,Tortora, Carola,Mellema, Indradevi D.,Tinnemans, Paul,Meekes, Hugo,Rutjes, Floris P. J. T.,Tsogoeva, Svetlana B.,Vlieg, Elias
, p. 839 - 844 (2020)
Viedma ripening is a deracemization process that has been used to deracemize a range of chiral molecules. The method has two major requirements: the compound needs to crystallize as a conglomerate and it needs to be racemizable under the crystallization c
Practical and Scalable Kinetic Resolution of BINOLs Mediated by a Chiral Counterion
Jones, Benjamin A.,Balan, Tudor,Jolliffe, John D.,Campbell, Craig D.,Smith, Martin D.
supporting information, p. 4596 - 4600 (2019/03/13)
BINOLs are valuable and widely used building blocks, chiral ligands, and catalysts that are effective across a remarkable range of different chemical transformations. Here we demonstrate that an ammonium salt catalyzed kinetic resolution of racemic BINOLs with benzyl tosylate proceeds with s up to 46. This is a scalable and practical process that can be applied across >30 different C2- and non-C2-symmetric BINOLs. Implementation of this method enables the enantioselective synthesis of a wide range of BINOL derivatives with over 99:1 e.r.
Fluxionally chiral DMAP catalysts: Kinetic resolution of axially chiral biaryl compounds
Ma, Gaoyuan,Deng, Jun,Sibi, Mukund P.
supporting information, p. 11818 - 11821 (2015/03/13)
Can organocatalysts that incorporate fluxional groups provide enhanced selectivity in asymmetric transformations? To address this issue, we have designed chiral 4-dimethylaminopyridine (DMAP) catalysts with fluxional chirality. These catalysts were found
A simple and regioselective carbon-oxygen bond cleavage using Niobium(V)
Arai, Shigeru,Sudo, Yukinori,Nishida, Atsushi
, p. 1104 - 1106 (2007/10/03)
A simple and convenient method for the differentiation of alkoxy groups on aromatic rings is described. Niobium(V) is found to possess a strong Lewis acid property to transform alkyl arylethers smoothly to the corresponding phenols in high yields. The excellent regioselectivity was also observed in dialkoxy benzene derivatives under mild conditions.
An expedient route to some monoalkyl ethers of enantiomerically pure bi-β-naphthol
Takahashi, Michiyasu,Ogasawara, Kunio
, p. 3125 - 3130 (2007/10/03)
An expedient route to a series of monoalkyl ethers of optically active bi-β-naphthol has been established by use of the Mitsunobu reaction.
Asymmetric Reduction with C1- and C2-Symmetric NADH Model Cpmpounds Containing Chiral 1,1'-Binaphthyls
Amano, Masaki,Watanabe, Motoshi,Baba, Naomichi,Oda, Jun'ichi,Inouye, Yuzo
, p. 3672 - 3678 (2007/10/02)
The present study deals with Mg-catalyzed asymmetric reduction of ethyl benzoylformate by the use of C2-symmetric NADH model compounds in which axial dissymmetry(chiral 1,1'-binaphthyl derivatives) was introduced as a chiral source for the first time and the results were compared with those obtained by the corresponding C1-symmetric models bearing the same chiral center.Better e.e.'s of the reduction product were obtained by the use of NADH models having C2-symmetry than does the corresponding C1-symmetric ones.Further, the kind of bonding as well as the distance between chiral binaphthyl and the reaction center affected the stereochemical course of hydrogen transfer.
