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Synthesis of Chiral Tertiary Allylic- and Propargylic Fluorides from Nonaflates of Chiral α‑Fluorinated β‑Keto Dicarbonyl Compounds

The acetyl group of chiral α-fluorinated dicarbonyl compounds was transformed to nonaflates through a reaction with perfluorobutanesulfonyl fluoride in the presence of DBU in 82–95% yield. These nonaflates were used in Suzuki and Sonogashira coupling reactions to afford chiral tertiary allylic fluor...

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Bibliographic Details
Published in:Journal of organic chemistry 2023-08, Vol.88 (16), p.11895-11904
Main Authors: Tomon, Daiki, Arimitsu, Satoru
Format: Article
Language:English
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Summary:The acetyl group of chiral α-fluorinated dicarbonyl compounds was transformed to nonaflates through a reaction with perfluorobutanesulfonyl fluoride in the presence of DBU in 82–95% yield. These nonaflates were used in Suzuki and Sonogashira coupling reactions to afford chiral tertiary allylic fluorides bearing gem-disubstituted terminal alkenes with excellent optical purities (45–91%, ≥94% ee). In addition, chiral tertiary propargylic fluorides were obtained from the reaction of nonaflates with DBU (73–86%, ≥94% ee).
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c01184