ol7b00246_si_001.pdf (8.44 MB)
Download file

Computationally Aided Absolute Stereochemical Determination of Enantioenriched Amines

Download (8.44 MB)
journal contribution
posted on 24.02.2017, 17:05 authored by Jun Zhang, Hadi Gholami, Xinliang Ding, Minji Chun, Chrysoula Vasileiou, Tatsuo Nehira, Babak Borhan
A simple and efficient protocol for sensing the absolute stereochemistry and enantiomeric excess of chiral monoamines is reported. Preparation of the sample requires a single-step reaction of the 1,1′-(bromomethylene)­dinaphthalene (BDN) with the chiral amine. Analysis of the exciton coupled circular dichroism generated from the BDN-derivatized chiral amine sample, along with comparison to conformational analysis performed computationally, yields the absolute stereochemistry of the parent chiral monoamine.