Configurationally Stable Biaryl Analogues of 4-(Dimethylamino)pyridine: A Novel Class of Chiral Nucleophilic Catalysts was written by Spivey, Alan C.;Fekner, Tomasz;Spey, Sharon E.;Adams, Harry. And the article was included in Journal of Organic Chemistry in 1999.Synthetic Route of C10H13BrN2O2 This article mentions the following:
A short synthetic approach toward a novel class of chiral nucleophilic catalysts, the dissymmetry of which stems from restricted rotation about an aryl-aryl bond, was developed. The key steps of the synthesis include preparation of a nucleophilic 1-methyl-2-pyrrolino[3,2-c]pyridine core by ortho-lithiation and creation of the biaryl axes via Suzuki cross-coupling reactions. Comparative HPLC studies of racemization for configurationally labile biaryls containing 1-methyl-2-pyrrolino[3,2-c]pyridine, 4-(dimethylamino)pyridine, and 4-(1-pyrrolidino)pyridine cores, resp., demonstrated that a pyrrolidino substituent ortho to the biaryl axis is optimal for slowing aryl-aryl rotation. Biaryls containing all 3 cores were shown to retain DMAP-like catalytic activity in the acylation of a hindered alc. 1-Methyl-7-(2-methyl- and -phenyl-1-naphthyl)-2-pyrrolino[3,2-c]pyridine, which are configurationally stable at ambient temperature, also were prepared via modification of configurationally labile derivatives These compounds in optically pure form should provide a useful starting point for studies on catalytic asym. acyl transfer using atropisomeric analogs of DMAP. In the experiment, the researchers used many compounds, for example, tert-Butyl (3-bromopyridin-4-yl)carbamate (cas: 257937-08-9Synthetic Route of C10H13BrN2O2).
tert-Butyl (3-bromopyridin-4-yl)carbamate (cas: 257937-08-9) belongs to pyridine derivatives. Pyridine has a dipole moment and a weaker resonant stabilization than benzene (resonance energy 117 kJ·mol−1 in pyridine vs. 150 kJ·mol−1 in benzene). Pyridine, its benzo and pyridine-based compounds play diverse roles in organic chemistry. Pyridine-based materials are valued for their optical and physical properties as well as their medical potential. Synthetic Route of C10H13BrN2O2