150766-94-2Relevant articles and documents
Stereostructure and thermodynamic stability of atropisomers of ortho-substituted 2,2′-diaryl-1,1′-binaphthalenes
Ehn, Marcel,Vassilev, Nikolay Georgiev,Kasak, Peter,Horvath, Branislav,Filo, Juraj,Mereiter, Kurt,Rakovsky, Erik,Putala, Martin
, p. 1303 - 1311 (2013)
A series of ortho-substituted 2,2′-aryl-1,1′-binaphthalenes were prepared via Negishi arylation of 2,2′-diiodo-1,1′- binaphthalene in good to high yields (65-95%) as an equilibrium mixtures of up to three atropisomers (unlike,unlike, like,unlike, and like,like). Thermodynamic stability parameters of the atropisomers were evaluated from VT NMR spectra by regression analysis. The DFT parameters calculated using CAM-B3LYP functional comprising solvent permittivity were, apart from the toluene solution, which was expected to interact with the aromatic solute, in qualitative agreement with the experimental values. In the case of the ditolyl derivative, the population of the atropisomers was confirmed by CD spectroscopy via comparison with the population-weighted averaged spectrum computed using the M06 functional. X-ray structure analyses of particular atropisomers of the dianisyl, dianilinyl, and dinaphthyl derivatives are also presented and discussed.
Cobalt-Catalyzed Oxidative Homocoupling of Arylzinc Species
Bourne-Branchu, Yann,Moncomble, Aurélien,Corpet, Martin,Danoun, Gregory,Gosmini, Corinne
, p. 3352 - 3356 (2016/09/12)
A novel procedure for the synthesis of functionalized symmetrical biaryl compounds is described. The reaction proceeds via the oxidative homocoupling of arylzinc species formed by cobalt catalysis in the presence of air or p-benzoquinone depending on the nature of the functional group.
α-C-Glycosides via syn Opening of 1,2-Anhydro Sugars with Organozinc Compounds in Toluene/n-Dibutyl Ether
Wagschal, Simon,Guilbaud, Johan,Rabet, Pauline,Farina, Vittorio,Lemaire, Sébastien
, p. 9328 - 9335 (2015/09/28)
The diastereoselective addition of organozinc species to 1,2-anhydro sugars in toluene/n-dibutyl ether solvent is reported. Compared to the existing methods, the reaction proceeds at 0 °C, and only a slight excess of nucleophile is required to achieve good yields. Scope was assessed with different O-protected glycals along with various nucleophiles (aryl, alkynyl). This methodology was applied to the synthesis of the α-anomer of canagliflozin.
