Title
Stereoselective Chiral Recognition of Amino Alcohols with 2,2′-Dihydroxybenzil
Author
Min-Seob Seo, Daeyoung Sun, Hyunwoo Kim
Year
2017
Journal
The Journal of Organic Chemistry
Abstract
2,2′-Dihydroxybenzil is demonstrated to be a highly diastereoselective stereodynamic receptor for the chiral recognition of amino alcohols. The receptor by forming diimine compounds with amino alcohols showed good (11:1) to excellent (>50:1) diastereoselectivity in chloroform. The existence of intramolecular hydrogen bonding with amino alcohols only in an axial conformer is demonstrated by 1H NMR and CD spectroscopy, X-ray crystallography, and DFT computations. The exciton chirality method can be used with diazo-attached 2,2′-dihydroxybenzil.
Full Article
Instrument
J-815
Keywords
Circular dichroism, Induced circular dichroism, Stereochemistry, Organic chemistry