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2,2′-dihydroxybenzil: A stereodynamic probe for primary amines controlled by steric strain

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Title
2,2′-dihydroxybenzil: A stereodynamic probe for primary amines controlled by steric strain
Author(s)
Min-Seob Seo; Ansoo Lee; Hyunwoo Kim
Publication Date
2014-06
Journal
ORGANIC LETTERS, v.16, no.11, pp.2950 - 2953
Publisher
AMER CHEMICAL SOC
Abstract
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. © 2014 American Chemical Society.
URI
https://pr.ibs.re.kr/handle/8788114/1020
DOI
10.1021/ol501088v
ISSN
1523-7060
Appears in Collections:
Center for Nanomaterials and Chemical Reactions(나노물질 및 화학반응 연구단) > 1. Journal Papers (저널논문)
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