S1 SUPPORTING INFORMATION DIASTEREOMERIC REISSERT COMPOUNDS OF ISOQUINOLINE & 6,7- DIMETHOXY-3,4-DIHYDROISOQUINOLINE IN STEREOSELECTIVE SYNTHESIS Harry W. Gibson, Michael A. G. Berg, Jennifer Clifton Dickson, Pierre R. Lecavalier, Hong Wang and Joseph S. Merola Department of Chemistry, Virginia Polytechnic Institute and State University Blacksburg, VA 24061 • General Procedures S7 • Chromatographic treatment of 2-l-menthoxycarbonyl-1,2- dihydroisoquinaldonitriles [(S)-8/(R)-8] S8 • l-Menthoxyacetic acid S9 • (-)-Menthoxyacetyl Chloride S9 • Aryl 1-isoquinolyl carbinyl l-menthyl carbonates S9 • Racemic 1-isoquinolyl phenyl carbinol (via 3, R = α-C 10 H 7 , R' = C 6 H 5 ) S10 • Racemic 1-isoquinolyl tert-butyl carbinol (rac-16)(via 3, R=α-C 10 H 7 , R’=tert-Bu) S11 • Optical purity analysis of isoquinolyl alcohols S12 • 1-Alkyl-2-l-menthoxycarbonyl-1,2-dihydroisoquinaldonitriles and 1-alkyl- 2-cholesteryloxycarbonyl-1,2-dihydroisoquinaldonitriles S13 • 1-Deuterio-2-l-menthoxycarbonyl-1,2-dihydroisoquinaldonitrile [(S)-8-d /(R)-8-d] S14 • Quenching of the anion from 2-cholesteryloxycarbonyl-1,2- dihydroisoquinaldonitrile [(S)-11] S14