861907-77-9Relevant academic research and scientific papers
The natural alkaloid isoanabasine: Synthesis from 2,3′-bipyridine, efficient resolution with BINOL, and assignment of absolute configuration by Mosher's method
Kang, Chuan-Qing,Cheng, Yan-Qin,Guo, Hai-Quan,Qiu, Xue-Peng,Gao, Lian-Xun
, p. 2141 - 2147 (2005)
A highly efficient and practical resolution of racemic 1- benzylisoanabasine, which was synthesized by reduction of the benzyl salt of 2,3′-bipyridine, has been achieved through molecular complexation with (R)-BINOL or (S)-BINOL to afford pure enantiomers (100% ee). The two enantiomers of the natural alkaloid isoanabasine have been obtained by debenzylation of the corresponding enantiomeric 1-benzylisoanabasine. Using Mosher's method by NMR techniques, the absolute configuration of (-)-isoanabasine has been assigned as the (R)-configuration for the first time. Moreover, an unexpected rotamer ratio of Mosher's amide was observed. The syn-form of two rotamers of (R)-MTPA-(R)-isoanabasine was predominant over the anti-form.
