S1 Supporting Information Computationally Aided Absolute Stereochemical Determination of Enantio-enriched Amines Jun Zhang, † Hadi Gholami, † Xinliang Ding, † Minji Chun, † Chrysoula Vasileiou, † Tatsuo Nehira, ‡ and Babak Borhan † * † Department of Chemistry, Michigan State University, East Lansing, Michigan 48824, USA; ‡ Graduate School of Integrated Arts and Sciences, Hiroshima University, Higashi-Hiroshima 739-8521, Japan Table of Contents: I. Materials and General Instrumentations:.…...……………………………………………..……..……..S2 II. ECCD Data for BDN-derivatized Enantiomeric Pairs of Chiral Amines:………………………… …S3 III. Reaction of 1-BDN with Chiral Amines:.…………………………………………………..……..….…S4 IV. Analysis of Enantiomeric Excess:.……………………………………………...………..………….….S6 V. General Procedure for Analysis of Absolute Stereochemistry of Amines:….………..……...….…S11 VI. Impurity Study:……………………………………………………….…………………......................S12 VII. General Procedure for CD Measurements:…………………………………………………...........S15 VIII. ECCD Spectra of 1-BDN Derivatized Chiral Amines:……………...............................…….…..S16 IX. ECCD Spectra of 1-BDN Derivatized Bn-protected Chiral Amines: …………..………………….S23 X. ECCD Spectra of 1-BDN Derivatized Chiral Amino Alcohols:………………………………....…...S25 XI. Synthesis of New Compounds:……………………………………………………….….……...........S27 XII. Quantum Chemical Modeling Studies:...…………………………………………...………..…..….S38 XIII. References:...…………………….………………………………………………….…...…....…..….S42 XIV. NMR Spectra:.………………….………………………………………………..……...…....……....S43