2,2'- Dihydroksy-1,1'-binaftyl (BINOL ) i jego pochodne. Wybrane syntezy i zastosowanie. Część I
Journal Title: Wiadomości Chemiczne - Year 2012, Vol 66, Issue 5
Abstract
1,1’-Binaphthyl and its derivatives represent a particular class of chemical molecules which chirality results from the restricted rotation about single bond of the two naphthalene rings. This generates the chirality axis. Therefore 1,1’-binaphthyl derivatives exist as two enantiomeric forms called atropoisomers. Moreover, 1,1’- binaphthyls with substituents at 2,2’ position exhibit higher rotational barriers around the 1,1’-axis, which affect a very stable chiral configuration. The classical examples of such molecules is 2,2-dihydroxy-1,1’-binaphthyl (BINOL ), which has become one of the most utilized chiral ligand and auxiliary for diverse asymmetric syntheses. The unchallenged success of BINOL and its derivatives in the field of transition metal-catalyzed asymmetric reactions or C-C bond forming reactions promoted worldwide an advancement of organic synthesis. The first synthesis of BINOL as racemate was described in 1873. Since then there have been found numerous efficient methods of racemic or enantiomerically pure BINOL preparation and its derivatization. In order to present a brief overview of the most convenient and facile routes to obtain racemic and nonracemic symmetrically substituted 1,1’-binaphthyls based on stoichiometric and catalytic oxidative coupling, classical optical resolution, kinetic enzymatic resolution of racemic mixture or regioselective modification of the binaphthol scaffold the following article is presented.
Authors and Affiliations
Dorota Krasowska
Kultowe bestie : literatura a nauka
Wampire, werewolf or zombie are individuals more and more often met in horrors. Since their existence seems to break down all rules of science literature experts consider them exclusively as metaphor of human anxiety tow...
Synteza i zastosowanie nowych katalizatorów metatezy olefin
Olefin metathesis has emerged as a powerful tool for the formation of carboncarbon double bonds. The success of this methodology has spurred the intense investigation of new catalysts showing a better application profile...
Reakcja Niementowskiego
The Niementowski reaction depends on the fusion of anthranilic acid with carbonyl compounds or amides and dates back to the end of the nineteenth century. Numerous variations of the reaction components and modifications...
Substancje biologicznie aktywne w winie
Wines are the subject of an increasing number of investigations. The benefits of red wine became widely recognized after the observation of “French paradox” [8–10]. It has been found that there is a low mortality rate fr...
Zastosowanie spektroskopii w podczerwieni w adsorpcji i katalizie (I)
The review presents some key results of infrared investigations of adsorbents and catalysts, which were obtained in Laboratory of Adsorption and Catalysis at Adam Mickiewicz University – conducted under the author guidan...