Bisoxazoline-Catalyzed Asymmetric Nucleophilic Addition of Diethyl Zinc to Fluorinated Alkyl Ketones: Enantiofacial Control by Changing the Bisoxazoline Substituent

Bisoxazoline (BOX)-catalyzed asymmetric nucleophilic addition of diethyl zinc to fluorinated alkyl ketones successfully afforded enantioenriched fluorinated alkyl tertiary alcohols. The effect of the size of the substituent on the oxazoline ring on the stereoselectivity of the reaction was investiga...

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Bibliographic Details
Published in:Bulletin of the Chemical Society of Japan 2015-01, Vol.88 (1), p.200-208
Main Authors: Sasaki, Shigeru, Yamauchi, Takayasu, Kanai, Masatomi, Ishii, Akihiro, Higashiyama, Kimio
Format: Article
Language:English
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Summary:Bisoxazoline (BOX)-catalyzed asymmetric nucleophilic addition of diethyl zinc to fluorinated alkyl ketones successfully afforded enantioenriched fluorinated alkyl tertiary alcohols. The effect of the size of the substituent on the oxazoline ring on the stereoselectivity of the reaction was investigated. Furthermore, the enantioselectivity could be reversed by altering the BOX bridge structure while retaining the C-4 substituent on the oxazoline ring.
ISSN:0009-2673
1348-0634
DOI:10.1246/bcsj.20140219