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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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Published in: | Journal of organic chemistry 2023-08, Vol.88 (16), p.11895-11904 |
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Main Authors: | , |
Format: | Article |
Language: | English |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
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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). |
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ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/acs.joc.3c01184 |