由手性α-氟代β-酮二羰基化合物的九氟甲磺酸盐合成手性叔烯丙基氟化物和炔丙基氟化物
Synthesis of Chiral Tertiary Allylic- and Propargylic Fluorides from Nonaflates of Chiral α-Fluorinated β-Keto Dicarbonyl Compounds.
作者信息
Tomon Daiki, Arimitsu Satoru
机构信息
Department of Chemistry, Biology and Marine Science, University of the Ryukyus, Senbaru 1, Nishihara, Nakagami, Okinawa 903-0213, Japan.
出版信息
J Org Chem. 2023 Aug 18;88(16):11895-11904. doi: 10.1021/acs.joc.3c01184. Epub 2023 Jul 31.
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 -disubstituted terminal alkenes with excellent optical purities (45-91%, ≥94% ). In addition, chiral tertiary propargylic fluorides were obtained from the reaction of nonaflates with DBU (73-86%, ≥94% ).
手性α-氟代二羰基化合物的乙酰基在DBU存在下与全氟丁烷磺酰氟反应，以82-95%的产率转化为全氟磺酸酯。这些全氟磺酸酯用于铃木和宗贺反应，得到具有优异光学纯度（45-91%，≥94%）的带有二取代末端烯烃的手性叔烯丙基氟化物。此外，通过全氟磺酸酯与DBU的反应获得了手性叔炔丙基氟化物（73-86%，≥94%）。
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