Asymmetric Henry Reaction Using Cobalt Complexes with Bisoxazoline Ligands Bearing Two Fluorous Tags

The effect of the presence of fluorous tags in bisoxazoline ligands on the stereoselectivity of the cobalt-catalyzed asymmetric Henry reaction was investigated. In contrast to the stereoselectivity obtained with conventional nonfluorous ligands, using bisoxazoline bidentate ligands featuring two flu...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2023-11, Vol.28 (22), p.7632
Main Authors: Ishihara, Kazuki, Kato, Yamato, Takeuchi, Narisa, Hayashi, Yuka, Hagiwara, Yuna, Shibuya, Shyota, Natsume, Tohya, Matsugi, Masato
Format: Article
Language:English
Subjects:
absolute configuration
Aqueous solutions
Carbon
Chromatography
Cobalt
Cyclopropane compounds
fluorous
Henry reaction
ligand
Ligands
NMR
Nuclear magnetic resonance
oxazoline
Solvents
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Summary:The effect of the presence of fluorous tags in bisoxazoline ligands on the stereoselectivity of the cobalt-catalyzed asymmetric Henry reaction was investigated. In contrast to the stereoselectivity obtained with conventional nonfluorous ligands, using bisoxazoline bidentate ligands featuring two fluorous tags in adjacent positions on the aromatic ring yielded a reversed stereoselectivity. The stereoselectivity also reversed when the fluorous tags were replaced with alkyl chains of equivalent length, albeit to a considerably lesser degree, highlighting the effect of the fluorous tags.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules28227632