4 years ago

Stereoselective Chiral Recognition of Amino Alcohols with 2,2′-Dihydroxybenzil

Stereoselective Chiral Recognition of Amino Alcohols with 2,2′-Dihydroxybenzil
Min-Seob Seo, Hyunwoo Kim, Daeyoung Sun
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.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00600

DOI: 10.1021/acs.joc.7b00600

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