124817-06-7Relevant articles and documents
A New Stereochemical Model from NMR for Benzoylated Cyclodextrins, Promising New Chiral Solvating Agents for the Chiral Analysis of 3,5-Dinitrophenyl Derivatives
Uccello-Barretta, Gloria,Cuzzola, Angela,Balzano, Federica,Menicagli, Rita,Iuliano, Anna,Salvadori, Piero
, p. 827 - 835 (1997)
Hexakis(2,3-di-O-benzoyl)-α-cyclodextrin and hexakis(2,3,6-tri-O-benzoyl)-α-cyclodextrin have been employed as chiral solvating agents (CSAs) for the NMR determination of the enantiomeric composition of derivatives of chiral amines, amino alcohols, alcohols, carboxyl acids, and amino acids bearing a 3,5-dinitrophenyl moiety. The conformational features of the two cyclodextrins have been carefully analyzed by NMR spectroscopy, and the origin of the symmetry change (C6 → C3), detected by NMR for hexakis(2,3-di-O-benzoyl)-α-cyclodextrin in CDC13, has been clarified.
Chiral Crystalline Sponges for the Absolute Structure Determination of Chiral Guests
Yan, Kaking,Dubey, Ritesh,Arai, Tatsuhiko,Inokuma, Yasuhide,Fujita, Makoto
, p. 11341 - 11344 (2017)
Chiral crystalline sponges with preinstalled chiral references were synthesized. On the basis of the known configurations of the chiral references, the absolute structures of guest compounds absorbed in the pores of the crystalline sponges can be reliably
A Straightforward Deracemization of sec-Alcohols Combining Organocatalytic Oxidation and Biocatalytic Reduction
Liardo, Elisa,Ríos-Lombardía, Nicolás,Morís, Francisco,González-Sabín, Javier,Rebolledo, Francisca
, p. 3031 - 3035 (2018/06/27)
An efficient organocatalytic oxidation of racemic secondary alcohols, mediated by sodium hypochlorite (NaOCl) and 2-azaadamantane N-oxyl (AZADO), has been conveniently coupled with a highly stereoselective bioreduction of the intermediate ketone, catalyzed by ketoreductases, in aqueous medium. The potential of this one-pot two-step deracemization process has been proven by a large set of structurally different secondary alcohols. Reactions were carried out up to 100 mm final concentration enabling the preparation of enantiopure alcohols with very high isolated yields (up to 98 %). When the protocol was applied to the stereoisomeric rac/meso mixture of diols, these were obtained with very high enantiomeric excesses and diastereomeric ratios (95 % yield, >99 % ee, >99: 1 dr).
Stereoselective reduction of 2-azido-1-phenylethanone derivatives by whole cells of marine-derived fungi applied to synthesis of enantioenriched β-hydroxy-1,2,3-triazoles
Alvarenga, Natália,Porto, André L. M.
, p. 388 - 396 (2017/10/06)
Several marine-derived fungi were evaluated by the bioreduction of 2-azido-1-phenylethanone 1, and the strains A. sydowii CBMAI 935 and M. racemosus CBMAI 847 were selected for the reduction of 2-azido-1-phenylethanone derivatives 2–4. Whole cells of A. s
