2,2 '-Dihydroxybenzil: A Stereodynamic Probe for Primary Amines Controlled by Steric Strain

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A rational approach for generating 1,1'-binaphthalene-like axial chirality of a small organic receptor, 2,2'-dihydroxybenzil is presented. The receptor combines with 2 equiv of monodentate primary amines to form a diimine, of which axial chirality is controlled by steric strain with moderate (1.4:1) to good (4.7:1) stereoselectivity. The observed circular dichroism (CD) spectra have been closely simulated by TD-DFT computations and can be used for determining the absolute chirality and enantiomeric excess of primary amines.
Publisher
AMER CHEMICAL SOC
Issue Date
2014-06
Language
English
Article Type
Article
Keywords

CHIRAL CARBOXYLIC-ACIDS; ABSOLUTE-CONFIGURATION DETERMINATION; CIRCULAR-DICHROISM SPECTROSCOPY; DIAZA-COPE REARRANGEMENT; INDUCED AXIAL CHIRALITY; ENANTIOMERIC EXCESS; SUPRAMOLECULAR CHIROGENESIS; RAPID-DETERMINATION; SECONDARY ALCOHOLS; GUEST STRUCTURE

Citation

ORGANIC LETTERS, v.16, no.11, pp.2950 - 2953

ISSN
1523-7060
DOI
10.1021/ol501088v
URI
http://hdl.handle.net/10203/192705
Appears in Collection
CH-Journal Papers(저널논문)
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