Synthesis and characterization of novel chiral derivatizing agents containing β-keto-anthracene adducts (KAAs) by ¹H-NMR: Aromatic influence and chiral alcohol absolute configuration determination

• Main Authors: Neeranuth Intakaew, Puracheth Rithchumpon, Chanatkran Prommin, Saranphong Yimklan, Nawee Kungwan, Praput Thavornyutikarn, Puttinan Meepowpan
• Format: Journal
• Published: 2019
• Subjects: Biochemistry, Genetics and Molecular Biology; Chemistry
• Online Access: https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85060013957&origin=inward; http://cmuir.cmu.ac.th/jspui/handle/6653943832/63584
• Institution: Chiang Mai University

© 2019 The Royal Society of Chemistry. New alternative chiral derivatizing agents, β-keto-anthracene adducts (KAAs), were accomplished and the influence of aromatic moieties at the α-carbon position for elucidation of the absolute configuration of chiral secondary alcohols via NMR was studied. The α-benzoyl substituted KAAs strongly enhance the anisotropic effect which produced greater ΔδRS values than other conventional reagents. We propose a simplified model to describe the conformations and to assign the absolute configuration in several chiral alcohol samples.