Access of cis-4-monofluoromethyl-1,3-oxazolidines via a formal [3+2] cycloaddition triggered by BF3•OEt2

[Display omitted] •We prepared cis-4-monofluoromethyl-1,3-oxazolidines from 2-monofluoromethyl-N-Ts-aziridine and a variety of aldehydes.•We confirmed the stereochemistry of the cis-4-monofluoromethyl-1,3-oxazolidine unequivocally for the first time.•The monofluoromethyl group (CFH2) is comparable t...

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Bibliographic Details
Published in:Journal of fluorine chemistry 2020-09, Vol.237, p.109599, Article 109599
Main Authors: Sato, Keiichi, Yamada, Yasunori, Hanamoto, Takeshi
Format: Article
Language:English
Subjects:
Aldehydes
Aziridine
Cycloaddition
Monofluoromethyl group (CFH2)
Organofluorine
Oxazolidine
Regioselectivity
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Summary:[Display omitted] •We prepared cis-4-monofluoromethyl-1,3-oxazolidines from 2-monofluoromethyl-N-Ts-aziridine and a variety of aldehydes.•We confirmed the stereochemistry of the cis-4-monofluoromethyl-1,3-oxazolidine unequivocally for the first time.•The monofluoromethyl group (CFH2) is comparable to those of trifluoromethyl and difluoromethyl groups in this type of cycloaddition. A series of cis-4-monofluoromethyl-1,3-oxazolidines were prepared from 2-monofluoromethyl-N-tosylaziridine and various aldehydes in the presence of BF3OEt2 under mild conditions. The high regioselectivity of the reaction suggested that the electron-withdrawing ability of the monofluoromethyl group is similar to that of trifluoromethyl and difluoromethyl groups in this type of cycloaddition.
ISSN:0022-1139
1873-3328
DOI:10.1016/j.jfluchem.2020.109599